Flat top roof not tall steeple easy to convert.

This is a typical roof drain.

New roof, siding, soffit, fascia, flooring upstair, repair fencing, yard work/landscaping, new flooring upstairs, new vanities, kitchen remodel, new paint job What was the outcome?

I have a great tenant and very few repairs issues (I put in a new HVAC and water heater a year before I moved out) but will eventually need a new roof (house was built in 2005). 

Year 2 had some large expenses, including some CapEx items (water heater, roof).

I also liked the fact that it was structurally sound with concrete block construction, a tile roof, and high elevation.

The other utilities will just come on when you change them to you, but you do want to be there right away to check for gas leaks.

For the first part of your question even if you were working with a realtor, I don't personally know many that have a true pulse on rehab costs and I wouldn't make any investment decisions based on their rehab cost projections.My suggestion would be to study how to evaluate the Big 6 rehab costs: roof, siding, windows, HVAC, electrical, and plumbing. 

Some will succeed at having a roof over their head.

What kind of roof is best for your area?