Looking for boats in Fla

[Eddiefuego]

I'm looking for my first big boat. YEHAAA

Now the bad news...I'm going crazy looking for my first boat.

I've got too little experience for what I"m trying to do, I've got less money than I need, and I'm in a hurry.

I bought my first boat 6 yrs ago...a Macgregor 26 trailer sailor. I'm in Iowa...so cut a little slack. We bought it to see if we like sailing. Well....HOOKED.

The plan now is to retire early...I'm 56...the Admiral is 53. The plan is pick up nice old boat that has been well cared for and set up. We'd stay in the Fla area this winter...likely in the Keys at a friendly marina and then learn the boat. After a year or two of working on the boat and learning to sail her we would like to coastal cruise the caribean and gulf, going down to perhaps the Rio Dulce for the following hurricane season.

My preference is for something that will stay above the waterline if I do my job, comfortable in a marina, can be single handed and I can get into it for less than 50K$. We'll be on a fixed income but able to handle expenses from what I've read. The plan now is to sail for 5 years and then sell...but we'll see then. I'd like to recoup my moneymy money...except for upgrades/maintenance at that time so I need to get something bought reasonably today.

I'm in Fla this week looking as a couple of boats and a couple of marinas. If you folks know of a boat I should not pass up...please ...I'm very open to suggestions.

I know a 5/8s from a 1/2 inch but would rather sail than fix...all the time...if you know what I mean.

Thanks for any help.
Eddie