I have a property to sell in Guilford, CT and I am training a brand new agent of mine to sell this - therefore, I am not looking for a listing agent.I'm aware that all the incentive for someone to help me may have gone out the window but I just want to be totally transparent! 

Renovations including converting a 2/1.5 unit to a 3/2 unit, increasing overall cashflow by an additional $1300 per month.What we bring to the table includes: negotioating, in-depth financial projection, in-house property management, and a strong, vertically integrated team of our attorney, contractors, CPA, and off-market suppliers.

And, as you already pointed out, the high LTV and PMI is a risk if you convert it to a rental property and the market takes a downturn. 

I would like to switch out the windows. 

The garage is enclosed and basically a bedroom, there is HVAC lighting closet , separate door etc, but no window.

You can convert 2 to 3 or 3 to 4 as long as zoning allows - with little consequence.  

Purchase price: $200,000 Cash invested: $200,000 Bought a twin house that was converted into a duplex.

Purchase price: $200,000 Cash invested: $200,000 Bought a twin house that was converted into a duplex.

We converted a personal residence into a rental seven years ago, our last tenant trashed it, we rehabbed it (repairs, paint, carpet) for about $8k but failed to sell it at an acceptable price. 

I know that I am looking at needing some pretty major repairs (new roof & windows) in the near future that are going to be large out of pocket expenses that won't actually increase the properties value at all.