. - Downtown location, near restaurants and a 3 min walk to train station- Only 2 off street parking spots, street is permit parking only but there is free parking down the street- Units have just been completely renovated- The city does not have any ordinances against short term rentalsThe biggest hurdles for me are: we're about to go into a slump/down season; potential parking issues; and if one of the other units were rented long term - dealing with the hassles related to that.

Lost days of work, had to cancel concrete trucks, etc...But I get the concept and agree in principle....but only for really important and potentially dangerous stuff...you wouldn't believe what I've seen out there.....

I always make it a point to emphasize to our new potential owners that they will earn more having us manage their MTR than if they self managed as a LTR.

I'm talking to a real estate lawyer tomorrow for some guidance, but in the meantime I'd really appreciate any advice about this situation, as I'm completely confused about what to do here.  

On the other hand, STRs present higher income potential, flexibility in pricing, and potential tax advantages, but require active management, adherence to regulations, and may entail unpredictable income.

Michigan might be a bit easier to start with because you may have more knowledge about the local area and market trends, but starting there could potentially slow down your move to Florida.

I live in Southwestern Connecticut, and am looking for places that are not only ideal for escaping the winter months but also have strong potential for rental income/future resale value of the property.

I’m thinking in terms of potential buyers passing on a property because they don’t want to deal with CMHA-related headaches?

@Hayden Thomas, I'm not a lawyer so don't take this as legal advice. 1.

Be sure to diligently evaluate potential properties through inspections, condition assessments, financial reviews, and property tax assessments.