Our mid-term in the south loop of Chicago is a 1 bed 1 bath about 550 square feet with no amenities...it's honestly perfect for the situation.

Cash flow very rarely exists in this market, so don't try to fit a square peg in a round hole.

Or, would my money be better spent someplace down south or by a National Park that would have year round traffic.My goal is to have a place where my family can spend a couple of weeks during the Summer, pad my retirement a bit, and have a place to leave my kids.Thank you in advance for your input.

Here's a quick summary:Manchester: STR demand could come from business travelers, especially near Hartford.Canton: Lower demand unless near outdoor recreation areas.Southington: Strong option with year-round tourists (skiing, Lake Compounce).Bristol: Good potential with ESPN and tourist attractions.Berlin: May have less demand unless near major highways.Focus on properties near attractions or business centers to keep occupancy high.

Anyways, even if a gap lender comes in, if it’s even an allowable second position (A lot of lenders won’t do that and Silent 2nds are a No-No) they add so much additional risk to the deal, potential legal ramifications and all around  generally dangerous feet’s.

Similarly, Houston has published statistics to highlight concerns with STRs: the city counts 10,545 short-term rentals and has logged 7,789 non-emergency 311 calls along with 61,167 emergency 911 calls within 300 feet of these properties from June 2023 to June 2024.

Over time I have dwindled that 300 owner list down to approx. 200 owners that I have sent 3 rounds of direct mail to this year.

It’s a great way to get your feet wet with less hassle.

At 1 community there is a year round contract for 3 bed-bug extermination heating units, year round, and there at work 24-7.     

@DemarquisMaybe initially see  if you can do a Joint Venture with an experienced investor to get feet wet