All sorts of little things you know if you are local but hard for outsiders to navigate. 

It ended up getting sorted out and the rent got issued through the CHMA, but there WAS a delay.

I have a CPA I work with who I’m sure will sort all of it out, just didn’t want to do something if it would cause a huge tax headache later.Do you know if you convert a STR to a LTR after a cost seg, will it cause a large repayment of taxes (I’m doing the cost segs to lower my W2 tax rate).

As the deal size gets larger, this should get lower. 

1) It's not unreasonable to end a tightening cycle with a larger rather than smaller drop.

Lastly, my initial goal is to house hack so I can theoretically live free for a few years, while buying multiple MFH to build a larger portfolio quickly.

I wouldn't recommend doing this with a property that is larger than 4 units as these do take more time than others.  

When repairing an existing home, there always seems to be some sort of a surprise... termites, underground plumbing, lots of wood-rot under the shingles, you name it... 

Why not give it a shot if your high school offers opportunities of that sort?

I'd like to use these to upgrade into something much larger in the next 2-4 years. 20+ units.