For example, when I get up to “estimating rehab costs”, for me it’s like it’s impossible to know how to estimate rehabbing costs without reading an entire book on it.

land has very little value if existing homes are selling for less than New build replacement costs. which is pretty much half of the US.. and especially in the mid west and rust belt areas.. building lots have value in dense urban areas where new infill is going on in a big way..

The reason for this is you are already being hit for these costs in your payment, so hitting you with the deduction on your returns would be double counting. 

What would you say the cost would be to setup and maintain this type of structure?

You likely need a much larger volume in lower cost areas to make the same money.  

However, where utilities are combined there is no easy way to estimate the cost because there are too many factors at play.

I hired a local handyman by father knew to 'save on repair costs' as opposed to going with one of my usual GC's.

I don’t see how you wouldn’t sell for $1M (let’s say net after all selling costs, because that’s how you have to repurchase.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

One cost to consider is downtime.