I’ve flipped a few houses and talked to a few investors and this is one of the biggest horror stories I’ve seen working with contractors.

Good question, I think the biggest question will just be your overall timeframe and how quickly you want to get everything done. 

The biggest indicator that they should not be comped against each other is from the market price of each.  

This is my smallest property but the biggest PIA to get lending on since I can't shop it to Fannie/Freddie and competitors.

In addition, if i used fixed rate financing, my biggest expense is fixed.  

Biggest thing here is they wants a house big enough for 2 separate living areas and house cannot have more than just a few steps to entrance and hopefully rear entry/etc.

Your biggest variable is going to be prop tax, and it changes from street to street. 

The biggest thing you can do is build your CORE 4 which consists of getting a great realtor, contractor, property manger, and attorney wherever you choose to start investing.Let me know how I can help you get going

Biggest mistake I see is going to vacation and then half of the 45 day ID period days are gone or an investor looking for a (deal of the century and not being realistic).

Identify the biggest losses and cut those with as minimal a loss as you can.