To keep or not to keep?

[Kameron Wilson]

I am coming up on the second year owning my primary residence, my question is whether it makes more sense to keep it and turn it into an investment property or take advantage of the appreciation and tax free money and use that to acquire other units. Here is the situation. 

My current house is 2/1 on about an acre, shared driveway, propane backup - rent would be around $1250-1400/ mo my PITI is $730.

I bought the property off market a year and half ago for 99,500 and i think i would sell for around 190k so roughly 90k tax free less 3% or so for buyers commission etc. 

I think the cashflow would be good but with the yard, landscaping, propane, and having a shared private drive if it would make more sense to take the 90K ish and use that for down payments on multis on smaller lots. Any input is welcome.