In this case, I think you're looking at the loser properties (because all the winners were sold quickly and often for list or more) and trying to draw sweeping conclusions about the state of a very complicated market.

If it is, the lender will have to appraise it - and that's a level of complication that you don't need.  

Otherwise, more complicated models, like the previously suggested NPV, IRR, DCF, MIRR are better suited. 

Its gets complicated if a mortgage is on just one of you guys and you guys have a loss.

Changing the properties into the name of the business isn't really an option, because quite a few of them have mortgages on them, and my experience so far with quit-claiming is that it just makes everything complicated with insurance, with potentially wanting to refinance or 1031 down the road, and besides that the local small bank that has several of my mortgages has no interest in accommodating this arrangement. 

I also like that I can work with a buyer and give them exactly what they want for finishing - I don't have to worry about making a bad design decision that isn't well-received by the market.On the other hand, contractually, this seems complicated and risky.

Turns out I'm in a single family zone...which certainly complicates going multi-family across both lots.

I spoke with a realtor yesterday and she told me that if I was to buy a house now, to rent out, that I may have complications getting a home of my own later on down the road due to me using my one first-time homebuyer tax credit.

It's not really that complicated to buy out of state.

My tax situation is slightly complicated-I'm a RE investor but also a self-employed musician and handyman so there's lots of business-related deductions; nothing too crazy but enough that I don't want to do it myself.