My tax professional is stating that I would need an appraisal to show the lot/structure are valued at $400k if I try to claim $200k as a donation.

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Maintain - includes taxes and insurance?

Most lower priced condo projects are not very healthy and why they are low priced.

A few weeks ago I wrote a summary overview to our investors in both funds to prepare them for probably lower returns in the short run from potential higher defaults.

At the same time, someone else reduces your debt, and you get to use the tax code to improve your tax situation legally.  

He was a good guy” and his information  on buying at tax or foreclosure sales was realistic and doable. 

@Rafael Ramos All your goals contradict each other:(1) Cashflow: buy Class C & D properties2) Appreciation: buy Class A & B properties3) Low Crime: buy Class A & B properties4) Why would you want your investments to lose money to lower your taxes?

How much money, after expenses and taxes would he property make yearly?

It would/could be only 15% capital gains tax and yes you could/would deduct all selling costs including commissions and transfer taxes.