They might be good markets, but then I lose the competitive advantage of knowing the areas as I rarely left the city. 

I could lose my job at anytime, but instead of trying to make it impossible for my employer to fire me, I budget, save, and invest so that the effects of unemployment would be less debilitating.

The point I was trying to make was that unless you already have a substantial nest egg, then you're just constantly losing and spending money and lenders won't like that

Does your PM really want to lose a client (you) based on something like this? 

@Michael ConteThat is a lot of risk and little reward.A) There is no guarantee that he will be eligible to obtain the mortgage to buy your house.It will ultimately depend on his credit score, down payment, DTI ratio, makes enough income, etc.He may lose business, he may be reporting no income on his return, etcHe may not want the house in 6 months.I would just move on.

Technically those funds are still tied to the original property, so if you invest them and things go sideways or south, you could be forced to sell the first property or lose it entirely. 

You could also “potentially” lose a bunch of money without consulting a market professional.

You'll lose the benefit on the next sale so deferring the tax for just a few months doesn't seem worth the effort. 

I’ve heard that people lose everything when they’re overleveraged.

I agree with losing another month and going with a good tenant vs the 2nd choiceThanks!