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 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?

Hi Griffin, It is not uncommon for hard money lenders to finance 90% of the purchase price and 100% of the rehab cost on a 6-12 month term, and then they'd be able to assist with long-term funding for the property once it has been rented.

It appears you purchased in mid 2020.  

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

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.

He'd be great to talk to if you are seeking an agent to help you find your first purchases. 

With greater appreciation, you can leverage that increased value through a HELOC or cash-out-refinance to purchase or rehab your next investment property.Where to begin?

I include non-paying tenants as part of the vacancy risk included in calculations I make prior to purchasing a rental to ensure it will cash flow.