If that fails I'll wait till its vacant, do some work and re-list/show/tour (safely)

A bit conservative, but that's what would allow me to be comfortable and feel that my family and home are safe. :) Good luck!

I might be inclined to share a little secret here... if your STR is currently in a Covid Zone: consider trying this: - Convert all listings to a 1 month minimum, by the room- Add all appropriate features to suit this- Mark the price up to 2-3x the typical rent, including everything- Sit back knowing that at 50% occupancy your roughly breaking even- Watch as your life gets really, really simple... as you have to work less and less every day, allow your net to drop to about 50% for a while, knowing that you are reducing the risk of Covid spreading in your business, and knowing that you are creating a safe space for those people who were planning to travel, but just want to chill while humanity finds a cure for this thing. 

If anyone has any advice for learning and being safe with contracts without spending weeks going through it with a comb greatly appreciated!

If you don't go this way, then I'd recommend you connect directly with a local general contractor, and meet them over there to discuss your concerns- permits, what's needed for it to be safe and functional and to code, etc.

I really see Columbus Ohio as an extremely safe bet for the next 10-20 years.

Based on the input of others in this area, sounds like $250/sf is a safe number to use for very rough analysis...

Most of the tenants in her building are very long-term as it is a safe, affordable apartment tucked in an expensive area, so they put up with the communal washer and dryer when they have to but most that live there have alternate options.

If the project you're buying has some salvage value in the event you can't get permits perhaps the answer may change a bit, but I would err on the side of being safe and passing if you can't get what you want to make you feel comfortable with buying the lot.  

I don't consider that kind of lock safe, it's a liability risk, and it may potentially interfere with my ability to access the apartment with notice or without notice, in the case of an emergency. 2) The lease states no pets without landlord permission.