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.

Let's discuss potential synergies and how we can forge mutually beneficial relationships for the long term.

The difference between CPAs and EAs is addressed  here (scroll down to my long comment on that old thread): https://www.biggerpockets.com/forums/51-tax-legal-issues-con...As to finding competent tax accountants, there are 20+ of us right here on this forum.

May I please get some confirmation from a real estate attorney on whether my full-time job qualifies under the IRA's legal definition of "real property trades".

Houston in particular be vary wary of flood zones and any potential historical water damage from the frequent flooding / hurricanes of just a few years ago. 

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

If you're doing it for legal protection, then you created an LLC not to manage the STR but to own it. 

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

. - 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.

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.