I'm sure everyone is familiar with the ads that show people lounging on a boat in some tropical location, drinks in hand and with no apparent care in the world. This is a lie. Don't believe it.
There is no such thing as the perfect sailboat. Boats are all about compromises, and a major compromise is in the time and effort it takes to maintain a boat. Don't be fooled by the myth of leisurely living on a sailboat, it is actually a lot of hard work and involves long periods of physical discomfort (imagine trying to sleep on a narrow, hard couch as it is violently tossed around the room for days on end, while someone squirts you and your bedding with salt water. That's often what it is like.) The leisurely moments are only rewards for long days and weeks of fixing things, sanding things, varnishing things, hauling things, and buying things. Lots of things.
Any used boat will involve quite a bit of maintenance and upgrades. I have seen even well-maintained boats becoming derelicts after just sitting in a slip for a couple of years, as gaskets and seals rot away, pipes and hoses dry up and crumble, as the relentless sunshine and humidity degrades everything onboard. Just keeping up with that a constant battle.
Relying on others to do the work is foolish, since no one will ever care about your boat as much as you, aside from the fact that finding a qualified and honest contractor is actually quite hard (never mind the cost!) I was well-aware that boats will require much more maintenance than planned, and that any project will inflate into a much larger one quite quickly...but the amount of work required is still quite surprising.
Boats require maintenance. I have yet to meet anyone whose boat is actually in perfect condition and required no additional work. Personally, I don't consider that negative at all, and in fact I enjoy working on my boat very much. More importantly, since the Master of any vessel (notice I didn't use the term "Captain") is always totally responsible for everything that happens on their boat, and since no one can really expect to get mechanical help quickly enough in case of an emergency while at sea, it is very important to get to know everything about your boat and how to fix any problem that may arise. Lives are quite literally at stake, and if something goes wrong, you can drown just as easily a few yards from land as miles offshore. Small issues can quickly add up to big problems. You need to be familiar with literally every wire, every nut, every bolt and every fitting - and you have to expect and be prepared to act when any one of these fails catastrophically in dire circumstances -- and there's a good chance they will. Fixing up a boat should therefore not be seen as a distraction but rather as a very important part of seamanship, because it is the only way to really learn your boat.
So in short, if you're in the market for a sailboat, make sure you know what you're getting into, and that you are willing to commit both the time and resources to manage a steep learning curve.
This is the only bit of moralizing you can expect on this blog, aside from an up-coming rant about drunks and careless boaters.