This can be done by using sites like AirDNA, or by clicking on Airbnb/VRBO and seeing what similar properties are renting for and how booked they are at what rates. 

Question is, should I go ahead and sell off all the properties now while I am still have a job and sell will be reflected on 2024 Taxes, them 0 income next 3 years.

Depending on our cash positions we may go ahead and do these, even though we don't plan to build for a year or two. 

Your other option is "pay by click". 

Simply Click this Link or go to http://www.biggerpockets.com/guest and fill out the form.Thanks in advance and we'll look forward to hearing from you.

I know one thoughts are “I can sell it for more” but that increases the risk as well because if I had a $250k loan on a $225k property and values continued to decline and the mortgage is in someone else’s name - I would be like “ok let me hand the deed back and walk away and go ahead and sue me…

As a complete newbie, I would have went full steam ahead with that $25k and bought something. 

Seems like a real cash cow if you get ahead of the ball. 

They should be leading the charge, explaining the process ahead of time so that you know they are large and in charge.Definitely look for a new PM.

I have the funds to pay for the roof replacement, and I would pay for it ahead of the actual purchase, but hate loosing on the tax depreciation on installing a new roof since I'll be paying for something I don't own.