Hence, your goal should be staying on the first page as long as possible instead of picking up a few bookings from different places.  

To stay secure, I’d recommend saving 3-6 months of mortgage payments, budgeting for repairs, and possibly investing in a home warranty.

I had to keep working, I have a cat, I could not stay at the property.

All I can say is stay away from Logic PM.

Quote from @Grant Woodward: Do you get pictures from your cleaners after every stay? 

I stay away from curtains as they can get dirty easily but I update the shades themselves to something nicer (plantation or shutter like shades or good quality roll down shades - black out in the bedroom).

If prices stay the same and I were to rent, I would be out of pocket for the entire HOA fee.

I’m curious - are you leaning toward staying local in Connecticut, or are you open to exploring oppurtunities in out-of-state markets like Phoenix?

Interview a few PMs, ensure they align with your goals, and stay involved by reviewing monthly reports.

My one suggestion: do not conduct business with anyone (here or anywhere) without having your lawyer and maybe even your CPA reviewing all the paperwork.Also, stay far away from LPs.