For HSA Receipt Savers

I believe you can split your HSA balance across multiple HSA custodians. In your situation I would be really tempted to keep the current account open with just a minimum balance to maintain access to all those electronic records.

I might have misspoken here. My current HSA custodian/administrator is JP Chase Morgan, which is transferring its administrator duties and accounts to HSA Bank. I believe the final details of this transfer will occur in June 2015 for account holders. I would hope that all electronic records and management tools transfer seamlessly. But one never knows until the ink is dried.

Last year was our first year with an HSA, but I decided to pay our routine medical bills with the HSA as we incurred the expenses. If we had a single multiple thousand dollar catastrophic expense, I might consider deferring that payment, but for little routine expenses saving, scanning, and spreadsheeting [-]dryer sheets[/-] medical receipts is just not how I want to spend my retirement. I remember the pain of managing capital gain tax lots when I had mutual fund dividends directly reinvested, and I also have a variety of illegible faded receipts originally saved for warranties. Add in the problems of the DW trying to figure out what to do with old receipts after I pass, our current low tax bracket, and it just does not seem worth it for me.

This is what is really driving me to start gradually paying qualified medical expenses from my HSA, especially since I think we will likely overfund the accounts, unless we're zapped by catastrophic illnesses or medical/dental problems not covered by our very good insurance coverage. I want to get it down to a manageable level so I'm hoping to reimburse myself for all of the qualified medical expenses we incurred in 2008 by the end of next week. It's not really that difficult for me to do this with Chase's Healthcare Spending Manager online tool, which I hope carries over to HSA Bank, the new custodian/administrator. If I don't do this and I predecease my wife, this would be a major headache for her.
 
> This is what is really driving me to start gradually paying qualified medical expenses from my HSA, especially since I think we will likely overfund the accounts

I don't know. There are a number of ways to spend money in an HSA even if you (or your spouse) have no records of previous medical expenses to use up:

- current year qualified medical expenses
- Medicare and other health care coverage if you were 65 or older

Worst case you can withdrawal money from an HSA after age 65 just like it's in an IRA - you pay regular taxes on the withdrawal. And there is no RMD requirement.

And since HSAs are a way to get money into an tax advantaged account even when you have no earned income, it's a pretty good deal.

The only downside I see is that if the HSA is inherited by a non-spouse it's counted as just a regular asset ("The fair market value of the HSA becomes taxable to the beneficiary in the year in which you die").

Publication 969 (2013), Health Savings Accounts and Other Tax-Favored Health Plans
 
I might have misspoken here. My current HSA custodian/administrator is JP Chase Morgan, which is transferring its administrator duties and accounts to HSA Bank. I believe the final details of this transfer will occur in June 2015 for account holders. I would hope that all electronic records and management tools transfer seamlessly. But one never knows until the ink is dried.
You've probably already done this but it's not a bad time to make sure you have up to date backup records.
 

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