I am considering purchasing a condo in Stamford, CT, to use as my personal residence, as I'll need to travel to CT frequently—about 50% of the time.

I am interested in purchasing a home that has been recently known as a squatter house. 

I know of at least 4 instances where investors purchased properties with agent representation that had intentions of doing an STR only to be denied a permit by the city after closing.Let me know if you have any other questions. 

Did anyone recently purchase a property there and hows the rental market?

It appears you purchased in mid 2020.  

The other thing it does is it makes you more useful to larger investors as you actually don't need your hand held and bring something more to the table.

We manage 100 rentals, mostly STR.Two options to consider. 1) With that low interest rate, it opens up possibilities to net a larger sales price with creative finance strategies like “Wrap” or “Subto.”2) You could sell and reinvest that $200k net into something that yields a stronger rental return, while enjoying the same appreciation over the next 10-20 years for the family legacy.

If I purchased the property how long, and difficult would it likely be for me to evict the squatter?

real estate syndicator specializing in larger multifamily communities in the Lancaster, PA, and Maryland markets.

In general, you will want 25% of the purchase price to buy the property, but you should also maintain a reserve to deal with unforeseen expenses like vacancies, maintenance, etc.Before you even begin, I think you should focus on a little education.1.