I’m still going through the learning what questions to ask phase.1) profits and losses?

You'll be viewed as having influenced the borrower and causing the loss, if you attempt to foreclose it then may appear that you did so to take a property.

Don't start buying the cheapest thing you can find, you'll end up spending WAY more- especially in a MFH, you'll be multiplying your losses. 

asset worksheets for each depreciable item - between 3 and 30+ pagessupporting statements for line items - between 1 and 10 pagesautomobile expenses worksheet - between 2 and 8 pagesForm 1098 worksheet(s) - between 1 and 4 pages per mortgagestate-specific worksheets, MAGI worksheets, passive losses worksheets, and a whole lot moreBy the way, including these extra worksheets will not create more work for me, they are already inside my tax software. 

Even though they didn’t collect enough to cover the total $35k loss.) and a week later I walked the property to confirm I was happy. 

So now instead of getting the deed, selling the property and helping to recover the losses from all of the redemptions, I end up still losing money on the liens that do not redeem.

If you want to have one, fine, but they are unnecessary for a small business model like yours, just another expense as far as I'm concerned.

Would you have net income or net loss without the cost seg study?

I know this is not ideal and I need to streamline into one PMS for future growth but am at a loss at what is available for different payout accounts to be associated with particular listings on OTAs. 

I would consider exiting if you could do so without a loss.