If you have a high end rental, you'll have more deposit and tenants will be concerned about having bad credit and won't likely just take off and leave you hanging with repainting. 

Wouldn't be a bad idea to buy some land close to the interstate and sit on it for a few years if you have the means. 

I'm pretty much debt free outside of my 2 mortgages so I'm not in a financial bind...but it just seems like a bad idea to pay so much for space I'm not using.

But it's not bad. 

I would be apprehensive on history of bed bugsI would say no if a previous landlord gave me a bad reviewand anyone in the world who threatens me out of some perceived moral high ground in an effort to intimidate me so they can get what they want at my expense, well they are surely to receive only my most vile behavior in return.I wouldn't just turn this person down, I would ask to meet in an empty parking lot and fist fight. but then again, that's just me, and I'm feeling particularly hostile today. real answer: you should pass, and stop communicating with this person

The banks want a bad property off of their books and it is easiest to work with them directly.

Is Vermont a bad state to be a landlord? 

Overall it seems like a lot of bad luck...how much longer can this go on before I hit a home run right?  

Many mistakes on my part plus a bad contractor).

I explained to him that I was a new investor and I could get a official contract, but he was done.That was my bad first experience but I'm not giving up.