Chris, now that you’ve confirmed it.

The condo doesn't have an elevator, but the other amenities are listed below:Amenities included: Common Grounds, Fitness Center, Gated, Reserved/Assigned ParkingServices included: Common Area Maintenance, Maintenance Structure, Insurance, Management, Pool(s), Recreation Facility, Reserve Funds, Snow Removal, Trash, Water, High Speed InternetThanks in advance for any advice!

I can confirm, the balance on the credit card reporting date is what counts, not the payoff date.

Do you keep a reserve?

The designated responsible party must be available on-site to address any issues as soon as one (1) hour following notification from an occupant, a city official, a code compliance officer, or law enforcement officer.Prior to the city issuing a certificate of registration, the vacation rental is subject to inspection to ensure compliance with: (1) minimum safety requirements under section 34.5-12; (2) minimum information requirements under section 34.5-13; and (3) to confirm compliance with Chapter 34.5 generally as well as any other applicable provisions of the Sarasota City Code and Zoning Code.The minimum safety requirements are set forth in section 34.5-12 and include compliance with the Residential Swimming Pool Safety Act, operation of smoke and carbon monoxide detection systems, and installation of fire extinguishers.The minimum informational requirements are set forth in section 34.5-13 and include, among other things, providing: (1) the location of the nearest hospital; (2) the non-emergency police telephone number; (3) the dates and approximate times of trash and recycling pick up; (4) the street address of the vacation rental; (5) the name and phone number of the designated responsible party or parties; and (6) emergency evacuation instructions.

You buy the property in an Entity, you must have at least 3-6 months or reserves.

Always have a cash reserve on hand, maybe twice what you think you'll need.  

Closing costs, expenses to make the property rent ready, and cash reserves add up to a lot more than you think.10-15 years for a FI goal is reasonable, but understand the snowball rolling downhill path of progress that it will take to get there.

How can I confirm that the tenant is paying on time and properly maintaining the property?

I've heard there is potential in certain pockets of NH however I can't confirm solely based on experience .