@Michael Kambic - there are many ways to accomplish your goals, but my first concern is that you're reporting your flips as capital gains. 

The few things that haven't are slowly getting extended before end of day.On the contrary, if a practitioner is slammed or very busy on April 15th I'd be concerned that he/she has poor engagement management and/or time management skills...I'm done with this thread... 

Yes we would definitely at least make a couple hundred once we moved out so that’s my main concern.

Have you talked to your agent about your concerns?

Once in a while I've called to see that the sewer is being paid.Through the years it's become a little harder to inquire if other utilities are being paid but the only one that ever concerns me is natural gas for units that have natural gas heat. 

I’m mostly concerned about CASH 💰!

Our concern is that if he wants to contribute, lets say 40k, that he would have to withdraw considerably more than that due to the tax hit. 

Given the use, I would want to see if there are any concerns with the condition of the property.

Many landlords are very concerned over the effect of the new Oregon law; 608.     

An overlay of shingles on the roof that I believe to be 10 years old (property was sold 2x in 2009 $53K then $110K) I am assuming all renovations happened then.There were other things that seem minor but these "structural issues" concerned the inspector.