I'm not an expert, but I don't think there is any way to avoid capital gains tax on this sale (short of moving to Colorado for two years) Your intention upon purchase doesn't change the fact that it's been a rental for all five years.

@Sherwin Vargas Take a deep breath.  

Even if he has good intentions, since we are not the keeper of ourselves, what if something were to happen to him?

White lies or intentional omissions are a slippery slope in business. 

Not kidding, either, though your words will be more elaborate and lengthy, the intent will be what I'm saying.  

In all honesty, I think rent control initiatives are very well-intentioned policies, that also garner a lot of political support, for reasons that can be very well understood.

I'll never change those people).My intention in starting the local group was for many reasons; inherently selfish reasons, if I was being candid. 

Actually I know I may be playing around thin profit margin but that's true my intention here is to learn.

LSF9 MASTER PARTICIPATION TRUST owns a few properties near me and would like to know their intentions. 

obviously when i bought it my intention wasn't really a buy and hold rental, but as i got older i decided this is something i wanted to do and figured since i already had the townhouse, why not start there.also- i know cash flow is looked at as a major goal of any buy and hold operation but just because the first property doesn't have strong cashflow, does that automatically make it a bad investment?