I called them out on it and even tried to convince the police that they should look at them for attempted fraud. 

The deed has been recorded, but the property is occupied and I have not been able to identify or reach the occupant.Here’s what I’ve done so far:- Knocked on the door while I was in Cleveland (I’m out of state)- Sent people 5 times to knock, doors locked from inside, car in garage, they dont answer- Posted a notice of new ownership with my contact information- Sent mail to the property- Attempted to reach the prior owner using case records (no response)The occupant will not answer the door or respond, even when there are signs someone is inside (car in driveway, door locked from inside).

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

I explain they will have difficulty renting a quality unit, that I will ding their credit, that I will attempt to garnish their future income to recover what they owe.

The ones that I attempted to sell are in Jacksonville, FL, North Charleston, SC, and Decatur, GA (Atlanta MSA).It's definitely more of a buyer's market for larger multifamily properties. 

I agree with you though - I am leaning towards starting with a local LTR before attempting a STR.

As others have already indicated, attempting raising rent to market has risks.

The maintenance fee is likely for funding/updating the funding over time as you acquire new assets such as the future LLC.In the end, it would almost certainly be better to work on funding your trust, whether you choose to use the firm that drafted the trust or attempt to do it on your own.

The numbers for tax/ins were an attempt to be conservative since I’ll eventually lose homestead exemption and need a different ins policy.

It would interesting to see if you could now vs my 2013 attempt.