Hi All,

About once a year or so, my wife and I start fantasizing about buying a condo near the ocean in Florida. She spent most of her adult life in Hudson (near Tampa), and my Dad used to own Captain Tony’s, and owned a 6-unit in Key West, so Florida is “in our blood.” We are 3 years from being able to travel more flexibly (daughter graduates), and our main source of income will be our 48 unit apartment rental business (unless we sell it, in which case our pile of cash will be!)

We like the ocean but understand that the insurance could be “crippling”, so we’re willing to be inland a few blocks. We anticipate that we’d be MUCH better off financially just renting via VRBO. So this is not a financial decision as much as an emotional one. For next 3 years, we’ll only be able to go down on school vacations (most expensive times to fly). Our primary reasons would be:

• Freedom of leaving at a moment’s notice and heading down & freedom to stay an extra day or three without worrying about the next renter being right behind us.
• Good “jumping off” place when we start traveling more. (i.e. it’s much cheaper to go on a cruise, fly to Ecuador, etc. from Florida than Maine. Maine is a horrible place to travel anywhere from (but a wonderful place to live)
• Having a place that has a lot of our clothes, supplies, etc. and forging relationships with the neighbors, etc.

I've often wondered if we could get a better deal / bang for the buck with a SFH. Yes, we'd need to handle hiring someone to look after it most of the year, but???

That all being said, I’d love to hear any thoughts y’all have, especially the “where?” Here is what’s important to us:

• Prefer ON the ocean (as in hearing the surf if we open our window) but will accept up to 10 minute drive from water’s edge. We’d live on canal, but would still want to be 10 minutes or less from SANDY beach.
• So sort of implied with #1, we want a sandy beach, not OVERLY crowded.
• Would LIKE to keep price to $250k or less but flexible as long as we’re convinced it’s a “no brainer” for eventual appreciation and ease of selling.
• Town where its somewhat laid back but NOT deserted. We’d like to be able to get to a few nice restaurants and shopping within, say 10-15 minute drive
• 2BR / 2BA minimum
• Must have pool & hot tub
• Reasonable condo fees
• Like to be able to rent it out VRBO style … could it be that if a HO assoc allows that, it might not be a great place to live?
• House vs. Condo? Compelling reasons to choose house over condo?
• Should be in an area that has a high chance of holding value, and being easy to sell in the future if we should want to.
• If we’re doing this on “want” vs. “need” I want to mitigate the financial damage by buying as intelligently as possible. So if there are any situations where we can get a discount for accepting “acceptable” challenges (can’t think of what those might be) we will. Maybe like a condo on a golf course, but the one farthest away from the course??

Perhaps a list of things we like / dislike would help too.

LOVE: healthy food, long walks, sunshine, laying by a quiet poolside reading. I would like to fish and snorkel once in a while, but one of my favorite things is long walks around 5 in the morning, especially on the beach. Our daughter is an avid English "hunter" style rider (horse shows), so it might be neat if horse ranch was nearby. 

DO NOT LOVE: Anything to do with golf, “botanical” gardens, fast food, poorly behaved children. (i.e. loud) We’d like to be far enough south that there is little chance of “enduring” a 55 degree week during the winter.

We’ve got friends with Condo in Venice and they speak highly of it. Also heard good things about Sarasota area … 

Thank you. I hope the way I presented all this is clear enough ... I sometimes use 5 words where one will do...