You could sell and 1031 it into the next property but you'd usually have to time the sale of your existing property and the closing of your new property right.I also wouldn't worry about having central air in the property unless that is essentially a requirement for you to remain competitive with the rest of that market.

If this election is made, the term “section 179 property” will include any qualified real property that is:Qualified improvement property as described in section 168(e)(6) of the Internal Revenue Code, andAny of the following improvements to nonresidential real property placed in service after the date the nonresidential real property was first placed in service.Roofs.Heating, ventilation, and air-conditioning property.Fire protection and alarm systems.Security systems.https://www.irs.gov/publicatio... 

He did a full renovation and in the process switched from a wall heater/central forced air unit to mini splits.

.- Both boilers installed new 2017- Both electric panels upgraded 2015  - Shared Backyard access for bottom 2 units- No Parking, No Central Air- House built before 1900- Roof about 20Yrs old- Assume Fed cuts rate at least .25 point later this year Any thoughts would be appreciated.

The university and the Air Force base are a continuous source of renters as well as incoming transplants.  

Assume a 10% (pulled out of the air number) interest rate on the heloc.

If you were looking to house hack I would recommend finding something that you could rent the top out as an air bnb (STR) and live in the basement with a completely separate entrance. 

I'm reaching out seeking some insights and advice regarding a rental property I currently have listed in Greenwich, CT.https://www.zillow.com/homedetails/33-Talbot-Ln-APT-3-Greenw...I have a beautiful 3-bedroom, 1.5-bathroom townhouse available for rent, featuring amenities such as central air, a spacious deck, a one-car garage, and an attic, along with one designated parking spot.

If not, sell it and move to another investment/market.I was in Honolulu last week and it was all over the news further tightening of Air bnb. part of the issues is the 9000 homeless after the Maui fire and owners not wanting to rent to those displaced..

I am Air Force currently stationed here in Fayetteville, NC.