I would recommend starting in your backyard and hone your skills if its possible, I know some markets have an extreme HCOL which may make it unfavorable in your case.

Hi Yael, I am a featured agent from Bigger Pockets in the QC market and can assist with all of your questions.

After 20+ years in real estate partnerships, here's what actually puts you on the IRS radar (and what doesn't):REAL Red Flags That Matter:The Partner Complaint TriggerDisgruntled partner files Form 8082K-1 disputesPartnership disputes leading to tax filingsReal Impact: Instant IRS attentionSuspicious Loss ClaimsLosses exceeding investmentArtificial basis inflationSudden large losses without economic realityExample: $100K investment claiming $500K lossesRelated Party GamesCircular property flipsBelow-market transfersFamily partnership schemes without substanceWatch Out: IRC §267 and §707(b) violationsDebt Engineering Red FlagsBasis inflation schemesArtificial guarantee arrangementsPartner debt shifts near year-endCritical: IRC §752 compliance matters!

Be sure to check out the free tools BP provides to help analyze deals you may have and also market insights.

Furthermore, @Dave Meyer has a YouTube show/podcast on market trends for your reference.

Since the house is for sale, the most important concern is marketability.

As with most municipalities and jurisdictions, the evolution of the AirBnB market has spawned regulation and restrictions on where, when and how a STR can operate.

Stay focused.4.Master your market.

Study the market.

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.