Either way I'm not really asking for Bernie Sanders commentary unless it is directly related to VT specific legislation that contributes to this.   

Titled the “More Homes on the Market Act” (H.R. 9015(link is external)), the legislation would double the capital gains exclusion for sales of principal residences from $250,000 to $500,000 for single filers and from $500,000 to $1 million for married couples filing a joint tax return, and also index these amounts for future inflation.

I know there have been redevelopment efforts through the City's master plan but I would like to know if there are any policies/ordinances/legislation that make the City easier to flip in.  

Have you read the legislation?

Don't be penny wise and pound foolish.That said, I'd be more worried about them legislating away your ability to STR.  

It was codified in CA in 1970 and has plenty of legislative and case law (over 47 years) to show how CA courts respect this right.How do you set these up?

So I'm hoping the recent effort to amend DF for seller financing works its way through the legislative process and loosens things up.Just wait for case law.  

This is the strategy I've found easiest to self-manage and what I have used exclusively since the city enacted STR legislations, addl taxes, fees, and licensing 2ish years ago.  30+ night stays are exempt that enforcement..STR laws are however host-friendly and it took a lot of effort by local hosts to get there.The crazy AirBnB parties where people get shot that you've read about in the news have happened here as well. 

It's basically corporate welfare.Once a couple of state legislators notice STRs in their neighborhoods, don't be surprised when they remove local control over STRs as well.I'm a 5th generation Floridian so I'm not going anywhere, but I've watched the quality of life take a nosedive, especially for the average Joe. 

Winters are brutal on the aging housing stock.Tenant laws in NY have recently swung and make it extremely difficult to evict tenants for non-payment.Combined Prop taxes are around 3.5% in the city.NY legislative body mostly interested in passing regressive (progressive) policy and making the situation worse.