It's not cheap

Sailboats are a lot to keep up and maintain, needing constant maintenance and neglecting it would only make its condition worse, kind of like children. And like children, you'll have inevitable expenses for as long as you keep it. And again like children, you'll be willing to pay because you love it. Cute metaphor, right? I think so.

So there are a lot of things to take into consideration. For starters, would I rather have a new sailboat or a used one. A new boat would have the advantages of being in top condition, squeaky clean, and of having a lasting warranty. The downside being that because it is new, necessary equipment would have to be bought (which can cost a lot to buy, like a trailer, life jackets, navigation electronic equipment, anchors and lines, etc.), and certain parts of the boat- like the sails- would have to be updated. A used boat on the other hand has the advantages of coming fully equipped and... well, that's pretty much it. Oh! And it is much, much cheaper than new boats. The downside would be that it will probably be pretty old, some equipment may need replacing, it may be damaged somehow (the reason for it being sold maybe), and limited or no warranty.
So what's my decision? I think for my first I'd rather have a used boat. If it was used, it was probably worth buying by the owner in its initial purchase. Plus it's cheap and all the equipment is there and ready. I think it would be cheaper anyways than buying a new boat because with a new boat I'll have to buy the expensive sailboat in addition to all the equipment and upgrades, while a used boat is cheap, would only have to replace a few items, and repairing it and bringing it back to good condition wouldn't be so costly, only a lot of work.

A used boat it is.

(boats can be to a few thousand dollars to up to a hundred thousand dollars :O woah!)

Monthly costs would be: insurance bill, loan bill if got a loan, repair and maintenance, docking/storage costs, and "surprise" extra costs. That's a lot, right? Right!