How do I gain confidence managing Daddy's bill paying? I work PT in my husband's business and manage my own home. It's a big load. Help!

No siblings for me because it is the Siblings finances I am trying to manage. And one thing that makes it easier is having things taken out of the account automatically, including the assisted living bill. I receive a monthly statement about this withdrawal.
A problem here is that you are in charge and NOT in charge. You have a mess you cannot address. I think you should either have Dad give you POA to manage his finances, or NOT. If not, fine. It is on him. If there is a serious dementia you may need to go for guardianship or public guardianship, and I will be truthful to tell you to think about which you want. If you get it it is ALL YOURS. And it will not be easy. The getting it straight with all entities where to send bills, what addresses to use for what, and etc. My wine box file doth overflow. It is a job. And no fooling. There are taxes. There is dealing with Social Security. There is just a ton of stuff. The fiduciary my bro and I considered before my taking this on (reluctantly at my 77 years of age) would have charged 90.00 an hour. THAT is not so bad, but my partner had an uneasy feeling about him, and that was more worrisome overall with my partner giving me the old one-two of "you owe it to your brother to keep all his stuff he worked so hard for safe".
So I would say this. Either DO this or don't. If Dad won't let you do the check book and the bills then sit it in his lap or ask for a court appointed guardian. They will like appoint YOU if you wish to serve. If you do not wish to serve they will assign someone who will be paid and then it is on THEM to keep Dad and his finances safe. Would honestly be my recommend. But up to you. I AM learning. After 7 months it IS getting easier and things are getting ironed out, but now my bro speaks of possibly moving home for a last try at independent living. And we are 3/4 of a state away and he is without support. And I cringe to think of more change.
Good luck. I hope you will update us. But don't allow this to be all willy nilly as you could actually end up in court behind trying to help and it going wrong. Too many chefs in your stew at present. Hugs.

Lots of good input from GardenArtist. Also, don't answer all his calls -- you need to put up boundaries. Either tell him politely that his constant calling is unnecessary and upsetting, or just don't answer all the calls. Maybe not even 1 every day. He'll get the message and you'll have more peace. Boundaries.

Dtr, if by "old school registry" you're referring to the standard check registers that are dispensed with checks, I find them hard to use just b/c they're so small.    So I just made up my own in Excel and printed it out.    I have a column for explanations as well.  It's worked fine for me and I can actually see what I'm writing!

If the financial advisor pays from the assets, I assume you're aware that each will decrease the remaining asset value.   (I'm assuming he has stocks, mutual, perhaps bonds or more complicated investments.)   Since he has income from other sources (farm and rental property), would those be adequate to pay the AL bill?  

Is the advisor a tax accountant as well?    Given that he has income assets as well as I assume a stock portfolio, and now I'm assuming monthly AL bills,  I'm wondering if she's integrated all the new factors into the mix.  

(I've never paid directly for AL; Dad was only on self pay as soon as he went into Palliative, then Hospice Care, so I have no familiarity with AL cost tax treatments.)

I think the first thing I would do is ask your father if he's agreeable to changing the delivery address for his bills and financial data, so that they come directly to you.  Then you can at least know what's incoming and what should be outgoing.   That made life easier for both of us.

You can always use a ledger or Excel sheet to display incoming and outgoing, and show it to him.  I also set up 1040 and Sch. A sheets and linked together.

You might, when you feel up to it, meet with his asset manager to review his portfolio and know what to expect and when, especially for long term planning.  As you're probably aware, speculations of recession exist, with what I consider the best ones predicting a recession within a year or so.

I assume you're already a co-signer on his checking account?   If not, are you considering having the asset management person be a co-signer?  Or, how would she pay the bills?   She will have to have some documented authority to access his checking account.   

My father executed his estate planning documents well before any illness set in, so I had contingent authority, but we always discussed things and worked out solutions.   When he began having difficulty writing (after losing part of his right hand to a radial arm saw), we discussed the issues and agreed that I would write checks and just keep him up to date.

As to anxiety over financial management, I do understand that.   This may sound trite, but all of my business files are in 3-ring notebooks, with front cover inserts of photos of flowers, which I cut from my gardening catalogues, & glue onto printing paper to make a floral collage. 

So when I pick up a Trust, tax or accounting notebook, I'm soothed immediately by momentarily being transported from being a bill payer to being a gardener, so I'm more relaxed when I tackle issues, especially trust and asset management issues.  This is especially needed for the tax files!  Sometimes I need a few chocolate bars for reinforcement as well.    

Personally, based on your assessment, I think that you have the capability to pay bills yourself once you get a system set up.  But I do understand feeling overwhelmed; it was a lot easier for me once I was co-signer, assessed the bill range and knew what and when to expect bills.   I still use that kind of checklist

Based on my own experience and that of others, nonparticipating siblings sometimes become too focused on asset management when another sibling is handling it.    Be proactive and protect yourself.   Even though your brother apparently hasn't challenged you on anything yet, that may change when your father passes. 

I apologize for being blunt, but there have been enough situations shared here to know what some siblings will do...want their share, and challenge if they don't feel money was managed properly.  

The first thing that comes to mind is the cost of paying someone to manage the bills.    So just think over this situation before making any changes.  

As to your father's multiple complaints, perhaps you can explain to him that you can deal with them, and the facility, more effectively, by addressing them in person, and more at one time.     Can he make a list of complaints for you, even dictating them if he has a smartphone or some tech device (I personally don't do this, but I'm trying to think of ways to consolidate the complaints)?

Then you can discuss them when you visit, identify potential solutions, and  address them, with the DON or Administrator, as appropriate.   It wouldn't hurt to have private discussions with them as well to get their input.   All parties are in fact in the solution circle.

He's probably feeling lonely and helpless; if you can involve him in the solution as well as the complaints, he may feel he's gained some control over his life.  I think that's critical for a successful adjustment.

BTW, is your father a Veteran?  If so, post back; there are a number of resources that are available,

Another thought.   The last 2 rehab facilities in which my father stayed (the last one also being where he had hospice care) had menus with selections, so residents did have choices in their meals.

You might check that out, and work with him to find something he enjoys.    He may be going through feeling he has to just accept what's available w/o any choice.   

If you can address his concerns, probably one by one, he may begin to feel more comfortable.

(I also went with my mother and father to events so they wouldn't feel alone.)

And do ask about pet therapy - it's critical for adjustment in my opinion.

Talk to daddy ONCE a day and that's it. Let the rest of his calls go to voice mail. If he has an audience for his chronic complaints, they will only get worse. He needs to speak with the staff at the AL if he has issues, and he knows that... he's just using you as a sounding board, as my mother does me. So WE make the rules and WE set the boundaries. As far as the food in AL goes, they ALL hate it, it's The Law....lol. Bring him some goodies when you visit and stock his fridge and cupboard with some of his favorites. That should cut down the complaining......not eliminate, mind you, but cut down.

Your father has good sources of income, it sounds like, so don't drive yourself crazy with spreadsheets and color coded notebooks to pay his bills. That's my suggestion. I worried myself sick over this very thing the first few years of being POA and only child for my elderly folks.

Nowadays I just do the best I can, as you are, without worrying about balancing checkbooks etc. Have you ever known the bank to make a mistake? Me neither. I can already hear the outrage others will express at this notion. Oh well. I keep an eye on the online accounts and write the checks monthly. I like your idea of having the investment counselor pay the AL bill each month. I have mothers investment guy automatically transfer a certain amount of money into my account each month so I can pay her Memory Care bill of $6400. Then I pay her random bills online with the debit card. If the money runs out, I'll apply for Medicaid, crossing that bridge if and when the time comes. Don't borrow trouble.

When I get nerved up, I ask myself the following question....does mother have enough money to live for the rest of this month? The answer is always Yes and that calms me down.

Best of luck...none of this is easy, I know

Thanks for the input. I am a signatory on the checking accounts, and I do have POA. He has some things automatically drafted from his account. It has been hard just figuring out his old-school way of entering things in his registry. My thoughts on having his financial advisor pay his AL bill each month was that she would set up something to draft it from his portfolio. I am just very hands-on with our finances and like to see where money is going and has come from. We still work, so I understand auto-deposited weekly paychecks, but auto-deposits of SS benefits and retirement don't gel in my mind yet! I can't even figure out when to post the deposits!

I recently created file folders to keep up with about five different categories of paperwork, and this is helping. I've wondered about having his mail forwarded to me, but it would be a huge deal to accomplish. We live on the same piece of property, so it's not hard to check his mail.

My brother has requested he be left out of anything that would be his after Daddy passes. He wants family land to come to me and to my children. After years of stewing over his absence, it was a huge relief to see this one act of generosity. He only asks questions and gives advice without knowing any of the circumstances. As sad as it is, he has promised to never contest any of the changes he urged Daddy to make in the succession of the property. It's weird, I know, and probably no one reading this would understand.

Thanks for the initial answers. I look forward to seeing more.