For me weather is a big deal. Also, I like to be able to eat outside at least half the year and I like to be able to do my zumba. I always recommend visiting a town before moving there and visiting the grocery stores and every day things you will be doing.
If you can live in a place that feels like vacation to you, I say do it. For each person that is defined different.
Obviously, you will want to look at the housing market (it is tough in a lot of places right now) or rental prices and other basic cost of living information.
I live in Central Florida, since you mention Florida, an hour north of Orlando. There are not many Spanish speakers in this area. Not like southeast Florida and Orlando. There are plenty of Spanish speakers in terms of being able to socialize with people from Latin America, our Spanish American club has 250 people show up every month to dance and socialize, but in terms of competition for jobs you would have an edge. At the university level you could look at University of Florida, or any of the community colleges.
The weather from about Vero and Sarasota (depending on the coast) and north is much cooler in the winter than southeast FL, so you do get a weather change and you will have to wear a jacket 60 days a year, but mostly just at night. Central Florida doesn’t really worry much about hurricanes. They get disorganized once over land and don’t pack as big of a punch, similar to some of what SC gets when they deal with hurricanes moving north.
If you are over 55 you might want to consider where I live! If you want to consider teaching at the K-12 level we have great schools in The Villages. I don’t know if the school here needs a Spanish teacher. There are also schools in nearby towns also that you can commute too, and a community college not too far actually. Many people who live here work at the schools or are retired professors and teachers.
No state income tax in FL. No sales tax on groceries. You will be closer to relatives. Nonstop flights to many places from Orlando Airport. gas prices vary around the state. My area is not very expensive.
I lived in Raleigh, and I found it to be only ok. I never felt at home there, but many people do, and there is a lot of universities in the area. I heard that Charlotte is great though. NC has fairly high taxes and they even property tax your car.
NYS is gorgeous, and I love it, but as mentioned, cold and snowy in the winter, you already know that. You don’t have to live as north as Rochester though. Stay out of the snow belt.
Virginia is a nice state, but also highish income taxes. Virginia would have very little natural disaster like concerns. The mountains would have very cold weather and snow, but near the coasts not so much. Northern VA near DC would be very expensive, and a lot of bilingual competition.
I actually liked living in the suburbs of Memphis, TN, but the one thing I didn’t like was higher crime rates. I would look up crime rates when considering areas.
I also think about the health care. Where I live finding a good doctor seems hit or miss, but I am about an hour from excellent care if I had cancer or something else that was serious.