My biggest concern with what you are describing is whether the restoration work was done properly, however I'm not getting enough information from what is here.

My biggest question is how or when do I liquidate.

Biggest challenge we face is finding employees who are motivated and eager to learn.

One of my biggest fears.

So the only way this number is going to change is if the appraiser admits they mailed it in the first time, they have 0 incentive to admit their mistake. 

We have owners who get their statement and immediately send the $400 or whatever the "remit balance" line says, which is unnecessary since rents have come in.What software are you using, and what are your biggest pain points with it?

As I have read, the biggest brrrr "fails" have been over-estimating the ARV (or just getting a bad appraisal) resulting in not being able to pull out all you put in.  

One of the biggest things I would do is sign outdoors, weather permitting (might be difficult if it's raining, with paper documents and all).

The biggest challenge we faced is booking them since they were pretty busy.

That being said house hacking is still an incredible tool and just because you don’t cover the full 100% / can’t quite cash flow positive you are still mitigating the vast majority of your families biggest expense while getting into an awesome business, building equity, having a shot at appreciation etc!