Just like doubling down on a bet you could lose it all. 

Now they are priced such that rates must go lower in order for the deals to work, and I'm not convinced that reality will support that bet.3.

I bet you would. 

Typically, you can only do one rollover per 12-month period (again, IRS Publication 969 has the details).In the end, having the option to invest your HSA funds is usually a better bet than letting them sit in a basic savings account.

I'd bet that this note is worth more to you than to most buyers until the note is much lower LTV, but I'm a novice in this space.

I bet both Columbus and Cincinnati made the list. 

Also, to track spending habits - just had a prospect withdraw their application when we asked why they were spending half their income on gambling websites.

Your best bet is to ask for referrals from professionals in the space: realtors, other investors, this forum, FB groups, etc.

Your best bet is in the midwest or southeast.

You do that, it's going to be best place to start because I am betting from there you will seek how to simplify things.