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Did you buy it as a long distance rental? Are you able to manage it effectively? Do you need money right now?
As Dave Ramsey would put it, would you buy this rental in NC today living in FL? If the answer is no, sell it. Sometimes, the hassle is not worth it.
Winston-Salem is a cool town. I love visiting, we go a few times a year for work but I’m not sure it’s the best market? I think there are some rough areas also some great ones. What part of town is it in?
That said, I’m a big believer in buying and holding as long as you can or at least until you know what you want to do with the cash from the sale. At the very least I’d hold it for 2 years so you don’t have to pay capital gains.
Yes, unless it was your primary residence and then was converted to a rental or vice versa, i.e., Year 1 & 2 primary, Years 3-5 rental, then sold for gain.
https://www.irs.gov/taxtopics/tc701
Doing a 1031 tax deferred exchange is also a possibility if you’re looking to keep the funds invested.