Team,Im having a tough time finding an insurance provider for my medium term rental in Pittsburgh and I'm looking for suggestions.I own the building (triplex) where 2/3 units are traditional long term rentals, and 1x unit is a medium term rental.

Nothing for you to worry about.How long has it taken you to get an offer? 

I would like to purchase long-term rentals (ideally in the Denver metro where I live) but am not sure what, if any, cash flow I could achieve. 

People much much wiser than I, always remind me, true wealth is built in the long-term.

I am now approaching 115+ days since assignment on my first 3 deals and because I am in NYS, my attorney tells me that I cannot even speak to buyer’s or seller’s attorneys due to “breach of contract”.I lost my first deal in fact because we were hindering on 130 days since assignment (should have been long closed) and the city decided to demo before we closed and were able to takeover in court. 

Since I cannot find a way to talk to someone over the phone on Zillow I contacted them about this via email, where every response takes a very long time.

If so, you can still wholesale the deal as long as the numbers make sense 

That's a decent area over there in Euclid / South Euclid, definitely not a D neighborhood, so as long as the property is in decent shape, you really should have no problem renting it out. 

Thats going to determine some of the decision making I'd think - you could always partially pay down the loan to achieve cash flow or breakeven or even a little relief - could be the best move if you think the property is well located and an otherwise good long term investment

Think long term!