If you wanted to retire and go all in I would stick to national credit grade investment grade BBB- or better tenants with minimum 10 plus years remaining on the primary lease term.

Hi Taylor,Free work in return for lowered rent might not be such a good idea.It would be Smart to go in person and see examples of the person's previous work (of the same kind you want done).I've seen (for example) gypsum board punched holes replaced that were  -->99.999% Invisible<-- and on the other hand, tub work by the same individual that was "childish" at best.I've had other instances of Handymen describing their work in various glowing terms, and according themselves with various (made up) glowing titles (master this, and certain grade experts)--claiming unbelievable past projects--who were no-shows or no-finishers.It's best to understand what the repair needs yourself, such as "Blue Board" or "Purple Board" and sealant XYZ vs just relying on statements such as I have done these for years--yes that may be true, but at what quality (if quality counts to you--it may not).You also may want to spec that you want the area left Broom Clean when the work is done, and make sure to provide a dumpster if there will be large demo taking place.Good Luck!

The fact that I'm doing this and not paying somebody else is largely a product of the fact that I want to eventually refinish the select-grade/clear oak floor and I cannot trust anyone to pull all those belt-shredding staples conscientiously for any amount of money.There's plenty of money down the line in fixing and bulletproofing the floor of the right rental, but I don't see people eagerly jumping at the bit to get at it.

We ultimately want to Buy (Land / Scrape Grade), Design, Build, and Sell.

I’m in at 90k+ with the house, he is in at 90k+ (Mid-high grade) on the rehab.

I'm not sure how they weight the different metrics to come up with their grades, but it's still a lot easier to use when compared to city-date.com or other sites like it. 

The most difficult one is that many of the cabins have "below grade" sq. footage/bedrooms/bathrooms and above grade sq. footage/bedrooms/bathrooms and you won't be able to tell by comparable listings the sq. ft above/below because they just aren't listed that way.Additionally, appraisers have to take 82 hours of required coursework and complete 2 years (I believe) as an apprentice. 

It really depends on the area and grade of home your are looking for.

House is located in on the slight grade hill.

As for info on Cleveland you're probably going to want to give The Ultimate Guide to Grading Cleveland Neighborhoods a read to get a lay of the land.