-June 2016 Sold-July 2016 Sold for same price-August 2016 Sold for same priceNow it's for sale again but listed quite a bit higher.Is this a huge red flag to stay away from it?

Big red flag... )-Have to approve every single repair request, no matter how small (for example if a tenant damages the closet door for the 3rd time in two months, obviously I'm not gonna keep having somebody come out, keep fixing it, and charging me)Are there property managers out there in the Cleveland, Ohio area that are willing to work with owners like that?

Honestly to me it's not the number of people that's a red flag, its the type of people.

The title searcher didn’t flag for restrictions or easements.

Any red flags I should be on the lookout for? 

I started with Stones River Property Management for a Singe Family Rental and already seeing some red flags.

Nothing brings out the NIMBY flag like a home newly purchased.Why not involve your siblings as partners. 

@David Khalfin, I went with the lower deductible as well on all three properties I've insured using that carrier.

Also, on the builders risk policy, there are carriers that will do a 12 month policy that can be cancelled earlier for a refund. 

Selling a house via quit-claim, and for only $2k, this really sounds like a red flag to me.