[Nothing here suggests he'd be charitable to you].

Your mission, especially if it's a charitable one, oftentimes will help raise the money for you.

Me thinks when you die your heirs can step up basis and start over. and then their are charitable remainder trusts that clients of mine have used for tax strategies..  

There are plenty of great pros here on BP, so if you're the charitable kind you could easily find some recommendations to pass along - or she could start her own account!

Did it provide her comfort to live in the home where her children were raised My long term plan is to have no debts at all in my golden years and use charitable giving to offset as much tax as possible. 

I charitably refer to it as a fully depreciated asset, which likely applies to much of the student housing stock in Madison.

You might consider a donor advised fund for charitable giving.  

plus your in recapture purgatory you get in you have one heck of a time ever retiring or exiting .this is why god and the IRS made Charitable remainder trusts.. one way to exit without getting hammered

I think we pay like $6500/yr is all, so SALT, car tabs, charitable contributions haven't been deductible for a while.Are most people (outside of the few really expensive markets) really paying more than $12k/yr in interest currently at 3-4%? 

This may create unrelated business income which could affect the charitable organization status of the church depending on how it is set up.That being said, I have a rental that backs to a Church - and the house next door is owned by the church and rented out.