In other words, how are you analyzing market trends, supply & demand, city's growth projections etc...

Hey Alex,Yea, scenes from Animal House run through my head when I get to thinking about worst case scenario hahaI will shoot you a message, as I am curious about your strategy and would like to know more. 

We ran into a few surprises during this time:Our lender, who had previously said we could use multiple sub-contractors through the rehab-loan process, changed their tune and demanded a single contractor be used.

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

Finding a place with high parking demand, but spread throughout the day, not all at once, proved too difficult for me at the time.

The area is saturated with 2/1’s for rent and not much demand.

Consider all three options, evaluate supply versus demand, and take action!

It comes down to supply and demand, and how motivated are you to sell your property? 

@Charlotte Casey our in house lender advised us that they are artificially raising their rates to slow the overwhelming demand for financing.

The very limited low down payment options demand higher interest rates and high mortgage insurance rates.