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.

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.  

I ended up sending an email with a notice to vacate with 45 days where he violated the lease term: "Tenant shall conduct himself/herself in amanner conducive to the peaceful enjoyment of the Premises.

-They handle all aspects of property management, allowing you to enjoy a steady income with no stress.Some Top Areas to Invest in Orlando:-Winter Park-Windermere-Winter Garden-East Orlando-OviedoEach of these areas offers a blend of amenities, a desirable neighborhood atmosphere, and property appreciation potential, making them prime locations for passive income investments.

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

The biggest advice I can give you is to figure out your own goals, and be specific, so I want to invest in multi family for cash flow for instance is too broad, is your goal to have an investment or a place you enjoy living, those are often in conflict as most multi family tends not to be in the most desirable parts of towns, are you willing to high cash flow in exchange for alot more effort, risk and limited appreciation, or do you want a more stable property with potentially less or even zero cash flow, if it’s a primary residence, are you going to live there long enough to make it more sense than renting, the breakeven period in a place like Baltimore might be 3-5 years.