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.

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.

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. 

I wouldn't go negative unless i was so confident I could take on that amount like maybe 50-100$ a month.

I think making it more generic and less custom is the safer bet.

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

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

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.

It's a stalemate due to affordability and either wages or prices give, I would bet the latter. 

Clearly, shes not happy and an unhappy tenant usually results in more issues down the road, and you can bet they'll be expensive issues.