#2 City Fheps has started making payments well above what the tenants owe.

Where would you start with $5000

The building might never be a total loss but you very well could have a liability claim big enough for the insurer to investigate that.  

If so, try starting with the median list price in your target market. 

If you don’t, then at least start with an appraisal and go from there. $145k sounds like a good starting point to me. 

I'm new to the area, and thought that joining CT REIA might be a way to start out.

But, it starts with choosing a market where you can afford to buy.Congrats on your home!!

Is he talking about cost based on what the total cost of the property would be over time, or just what the total cost of the property would be to the REI over time? 

If you prefer to have the MMLLC involved from the start, consider a "drop and swap" strategy, where the property is moved into an LLC before the exchange, though this requires careful timing.

My family and I recently relocated to Orlando where we also started a Vacation Rental Property Management company.