Revenue stream.  

If you're seeking a reliable income stream, you should definitely consider Cleveland.

Secondly, a would like to produce a good stream of cash flow to help me scale (as I'm assuming most are looking for). 

I would highly encourage paying a GC to walk deals out the gate, have them give a scope of work so you can see what items costs.

There are two items that you need to completely solve this problem for your rehabs: properly built Design Boards and a Finish Schedule.

Another struggle i have with STR is replacing small items continually which ties back to pricing.

I think you will definitely want to talk to your lawyer because there may be items linked to this transaction you are not considering. 

The property taxes will be on his Schedule A during the time the property was his primary residence, assuming he itemizes.

Creative ApproachesIf the organization is hesitant about a sale, consider proposing creative terms:Seller Financing: The non-profit could retain an income stream from the property by financing the purchase.Partnership or Lease-Purchase Agreement: Offer to lease the property with an option to buy, giving them time to evaluate the relationship.Donation or Support: Consider including a donation or offering support for their mission as part of the deal.

True the new owner will have to start his own account, but he should have a built-in revenue stream from repeat guess that will search for that property by address.