Most of my clients look into areas like Old North, Old Town East/King Lincoln-BronzeVille, Merion Village, Driving Park, North Linden, Hungarian Village, Bexley, and North Hilltop.I created a neighborhood grade map that I can share with you. 

What you buy in each of the markets will play a bigger role in which market you choose. if you want more info on the Cleveland market give The Ultimate Guide to Grading Cleveland Neighborhoods a read.

No, DONT make it a per month number that's novice to point of grade-school, set a whole $ amount by yr 5 that is upward desire and minimum required.

If so, are there any restrictions (i.e occupancy, market grade, etc, if DSCR is below 1.00x, etc.)- Can you underwrite with historical booking history?

  $5k isn't close to realistic.By the time you add up grading, foundation, sewer (with fall), water, low voltage, and access-related changes, I would expect something on the order of $20k in horizontal costs for a typical flat 5000sf lot to drop one of these in the backyard. 

I also bought quite a few 20 40 80 acre tracts and would bust them up as well.. it was pretty cool because in Oregon logging permits are a snap.. you dont need any county grading permits to bust in your logging roads so say I had a 20 acre that I was going to short plat into 4 5s we would put the road in the logical spot for each parcel future access and then put a few landings in the logical spot for the homesites all under logging permits saved THOUSANDS .. then sell off the lots..

Per my understanding, that means a 2400 sq ft lot would allow at most 2160 sq ft of finished, above grade indoor space. 

Check out The Ultimate Guide to Grading Cleveland Neighborhoods before spending any money on a BRRRR deal.

I have my electrical and hvac guys buy everything as soon as possible once i get my grading permit. 

That's a win for me, I dont think that $200k would be enough to turn that building into a condo grade property and you'll like need to dormer because of the pitch of that attic.