You want to focus on places with reasonable fees, avoid high rises, make sure they are warrantable, make sure the condo association is in good financial health. 

Even if you win the eviction you need to then get a lockout date set and a warrant of removal.

PITI looks like $920.25 based on your numbers above, definitely warrants a further look depending on amortization/term of the loan from your family member. 

If not, I'd simply move on, but if you can and/or the seller would be flexible on a lower price, it may warrant a second look.

Needless to say- I got no packages/mail forwarded.I can also update that I consulted with two lawyers (one through a free service my job offers, kinda like legal shield lol, and the other is my closing attorney), they both agreed it is not a serious claim and doesn't warrant a response.

I am hoping to get opinions on if the business has matured enough to warrant the desire from a private investor to make this type of investment without having to leverage my personally held assets or credit etc.

Early estimates for a cashout refi would put our monthly payments (PITI+HOA+PMI) up from ~$2100, to around $2500-2600 and we could potentially lower our interest rate by 0.25% (I’ve been advised this % drop doesn’t typically warrant a refi).Very appreciative of any thoughts or insights folks can add to help me round out my thinking and fill in any blind spots!

The typical Arizona residential contract has a provision "Buyer warrants that Buyer has disclosed any information that may materially and adversely affect Buyers ability to close escrow or complete the obligations of this contract"Placing multiple offers without the ability to purchase multiple properties is risky and has resulted in lawsuits so it's an area to be very careful.

However as long as there aren't complaints that are substantial enough to warrant the county doing an inspection, you will likely be fine renting both sides.

I have no doubts that some of these section 8 tenants have caused trouble and your displeasure is warranted.