Hey BP, would love your advice!

My wife and I along with our 19mo old are looking to move. We currently live in Waunakee (right outside Madison, WI) and looking to move to Venice, FL to be close to retired grandparents. 

I am a Realtor so this will play into the figures below. 

We currently live in a very sought after town with top 5 school district in the entire state and live in an extremely sought after neighborhood. I only mention this to lay the groundwork for our decision. 

Bought 3 years ago for $340,000, put 10% down, owe $291,000 and house valued at $415,000 right now if we sold (did many updates, though still needs more)

If we sell now, obviously we would save about $12,000 in listing fees because of my Realtor job. 

If we rent it out, there are about 3 rentals in our neighborhood and all rent for avg of $2850. We have a CEO of a company wanting to rent our place to get his children into our school district and wants our neighborhood as his daughters already have friends here. Possibility he would buy it but 80/20 he rents. 

Our mortgage, insurance, taxes comes to $2,050 a month. 

Obviously we have lots of equity in the place and if we rent we'd be cash flowing pretty nicely. Never been a landlord yet, and then to do so long distance would be a new challenge, and one I would be ok taking on. We have a cabin up north of here so I would be coming up here frequently from FL to go there and would do updates, and check on the place when needed. 

Any opinions from people here. I value everyone's thoughts, hence why I posted figures for a more precise answer. 

Im caught up on listing now and saving $12,000 in fee's and taking the money and running. Versus renting it and maybe selling it in a few years and paying more in fees as I would not be a local Realtor anymore. I did NOT account for appreciation as that would just be a cherry on top. 

thank you all!