For instance if I’m looking at potential capital expenditures over the next 5 years and the range of the cost is between $25k and $75k, I would use $75k in my projections.

I won’t sugar coat it when I first got in I didn’t realize the over head cost to run a business .

What is your price range and what do you consider to be a "medium" rehab project, rehab costs = to 25%-50% of the purchase price?

Selling and buying something else you want keep and doing a cost seg in would help with the tax burden probably better in this situation.

Kudos to you for doing something to create a secondary income stream. there are 5 income streams in RE rentals, possibly six if you do things a certain way.The reality here is your model (buy box) is suffering from too high an entry and too high a cost of capital.

Most won't insure pools with diving boards or ones without a VGBA drain.2) Include the cost of a pool company to manage the pool in the rent. 

In the beginning I want to manage by myself to save cost.

This, on top of the up to 17% cost of capital.3.

Total cost of land and size?

My gut feeling is it's going to cost around $4,000 to repair and has been there for ages.