I understand all that, but what throws me off is that the house was previously assessed to be lot higher, and then when the previous owner came in, it was cut in about half...and then now that they fixed up the place and sold it to me, looks like the assessment went right back up.   

or other structural warning signs like large notches cut out of floor joists to run conduit? 

Pretty sure they are straight forward, but if you only have 2 months of history, I am sure we can work with that as they will finance new STR with no history.Cheers!

To be clear, I’m not afraid of IRS as all of my records are straight, but I’m not a fan of Apts.com using this strategy, so I will start looking for alternatives.

I do not invest in townhomes or condos as the HOA dues cut into your cash flow, you have to deal with the rules and regulations, get permission from the arch committee to do anything, and in down markets, they lose the most the quickest.

You win by buying right, not cutting costs/corners in repairs.

If it were me I would cut that bill unless that's the only way they could have access.

That cuts to the core of how and why Zillow did what they did.

If your goal is to be a real estate investor, then I highly recommend you learn/study/live an actual RE investing strategy like buy and hold (which can be straight landlording, house hacking, BRRRR) and can be done in single family or multi family or you can flip or develop properties (but that too is a job and income stops when you stop flipping).Not to discourage you from your wholesaling desires, but think long and hard as to how and why you came to such a decision and know it is NOT RE investing.

I do give advice frequently, but I try to be a straight shooter and not give advice if I am uncertain.