The first bit of advice is: do your homework first. Follow the guide below and then form an idea of the makes and models of boats fit your requirements. If you know what boat fits your requirements now, you can jump on a boat immediately, avoiding missing out on a bargain.
The first golden rule is avoid a boat that contains any wood. Do not buy a boat that has wood in the construction of the hull or topsides, EVER! It will bankrupt you. Seriously. It will rot even while you are trying to fix it, the inconsiderate bugger.
Wooden boats are for those with big budgets who can pay a yard to fix it, or people with good woodworking skills and lots of spare time. Both can get a wooden boat up together quickly, beating the rampant rot.
So we come to Skint Sailor rule number 1:
DON'T BUY A WOODEN BOAT OR A BOAT THAT CONTAINS WOOD IN IT'S CONSTRUCTION!
Now we have the first rule established, it means that we're looking at an ALL GRP boat. There are some boats out there that started as wooden boats and then went to GRP and some that started as hybrids and then went to all-GRP. If you see a boat, do your homework and make sure the boat is all GRP.
Good, the material is established, now lets concentrate a bit on the design of the ideal skint sailing boat.
The preference is for a twin or triple bilge keel boat. Twin is better because there is less drag, triple keelers add an uneccessary extra bit of underwater gubbins. Why a bilge keeler I hear you ask? (or maybe it's the voice in my head).
Well, a single keeler cannot take the ground on it's own. Out of the water it needs beaching legs, or a cradle to stay upright. It also means a full tide mooring where the boat is floating all the time. Full tide deep water moorings are more expensive and cradles need hiring when you get the boat lifted out of the water to work on it. Lifted? that means more expense paying crane fees.
Nope, that's all a bit to complicated, unnecessary and expensive for the Skint Sailor. If you need to scrub off the bottom, just run a bilge keeler onto a beach and wait for the tide to go out. Like this:
You really, really need to put it on the hard in a yard? It just sits on the floor, with no need to hire a cradle.
An alternative is a lift keel boat, but in small boats lift keels usually mean compromising internal space to accommodate the keel box. It's a layer of complexity that is unnecessary and tends to seize up if left on a mud mooring. Great for trailer-sailers, you might think sticking the boat on the drive saves money, but you'll have to pay each time you launch, pay extra for the trailer and also have to maintain that trailer too.
Also be wary of the rudder arrangement. A rudder with a stem through the hull and no skeg is very vulnerable. This could happen to an unprotected rudder:
Not easy to repair and just adds another hole in the hull. So Through-hull rudder with skeg only, otherwise a transom-hung rudder. And make sure you remove the transom-hung rudder and put it in the cabin for safethy and security. Jim has lost 2 transom-hung rudders now after leaving them in place.
Skint Sailor rule number 2:
BUY A BILGE KEEL BOAT OR ONE THAT CAN TAKE THE GROUND EASILY.
So, we've determined the ideal boat is made of GRP and has two or more keels so it can take the ground easily.
The next bit is size. Big boats are great, you get full headroom and usually a permanent toilet installation. Luxury. But..... with a bigger boat comes bigger bills. Anything over 24ft or so starts to go up a level on mooring fees, it means the insurance company needs a survey before they'll insure it, it can also man an inboard engine, which is a magnitude higher in complexity than an outboard.... through-hulls, stopcocks, wet exhausts, stern tubes.... all those things that give inboard owners sleepless nights disappear with small boat with an outboard.
Also a bigger boat incurs higher fees every time you stop at a marina, or use a service at a marina.
When it comes to Marinas, with a shorter boat you have more of a chance of getting a space, as the Marina can put you in a small nook somewhere like this:
Skint Sailor Rule Number 3:
KEEP TO UNDER 23FT IN LENGTH TO AVOID EXTRA COSTS.
I've already mentioned the extra complexity with inboard engines. They are always more expensive to buy than outboards and you have to call the mechanic to your engine with an inboard. With an outboard you can take the engine to the mechanic, saving call-out costs.
The only downside of outboards is they don't run on Diesel, so fuel isn't cheap because you end up buying road fuel with road fuel duty added. You can get red diesel cheap and diesel engines sip fuel.
So inboard and outboard engines have different pros and cons, but on balance the outboard is cheaper in the long run.
Skint Sailor Rule Number 4:
GO FOR A BOAT WITH AN OUTBOARD ENGINE.
The next consideration is when to buy your boat. We all know that what we laughingly call a summer is the the height of the sailing season and prices are high at that time, but when do prices drop?
The first price dip of the year is February/March. Most sailing clubs, Marinas and Harbour Masters collect their yearly fees at that time, so owners desperate to avoid paying a further 12 months worth of fees will want to offload their boat. So that's the first drop in prices.
The second drop is after the sailing season closes. Maybe an owner hasn't been able to use the boat in the summer and decides to sell up before the really bad weather closes in.
For the brave (and heartless), there is always Christmas. Its a good time as people sell to pay for pressies and no-one else has money, so you can pick up a bargain from a seller desperate for money to buy the kids that must-have toy and avoid looking like a heartless monster. Also at Christmas desperate people put boats on eBay. Most of the competition has maxed out their account so there are fewer people out there with money to outbid you.
Other bits of wisdom are:
A floating boat beats one on the hard.
Mainly because you do know it floats. A boat on the hard hasn't proven itself watertight (even if it's full of rain water) so one that is floating and appears to have done for a while is a better prospect.
Free boats are out there.
I got Sprite from a Freecycle ad. Technically she cost me the price of the engine, but I still maintain I paid for an outboard and the boat was thrown in for free. ;-)
Other sites like Freegle, Trashnothing and the free groups on Facebook are worth joining to keep watching for free boats. Just don't have high expectations. They'll need work, but don't forget if the boat is free you can possibly get it up to scratch usually for a lot less than the boat is actually worth. Three years in and I still haven't spent the money on Sprite equivalent to what I'd get back for it if I sold it.
If you can't get a a free boat, get a cheap one.
Also if you see a boat in eBay that you like the look of but got outbid on, keep it in the back of your mind. If it comes up again, then the seller has been let down by a buyer. I've seen boats go on eBay several times and come back again and again. It may be worth pinging the seller a message with a firm offer (lower than the previous final prices and within your budget obviously). They may go for it if they have genuinely been let down by dodgy buyers. Or they could ignore you if they've have friends making fake bids and trying to run up the price.
Another thing to note is that boats in yards tend to attract a premium price. The owner is generally still paying yard fees on the boat so understands it has some value. Usually an over-inflated idea of the value. Boats in yards that have been abandoned by their owner and offered in lieu of yard fees by the yard owner may be worthwhile if they aren't full of rainwater and all the bits are present. I've seen plenty offered without interior cushions (expensive) and/or sails (very expensive) and/or masts (very, very expensive).
Don't forget to check any hidden costs for yard boats. The yard will usually charge to lift the boat onto a trailer or into the water (often they say a free lift is available just to get shut of the thing, but check first, especially if they don't explicitly say a free lift is included) or to get a boat out of a secluded corner of the yard. I think they'd take a dim view of you moving half a dozen boats to get the wreck out of the corner.
Boat club boats that are for sale and have been lifted out for the winter will usually have to stay there until the spring. You might get stung for yard fees, storage, boat club membership or other costs. Again, check.
Finally harbour masters advertise boats on eBay. Shoreham is one port authority that offers guano-encrusted abandoned boats for sale usually every Spring and Brighton Marina offer abandoned boats on a regular basis. Quality varies considerably and the majority tend to be fin keeled, so not for the skint sailor.
You Need Plenty of Luck.
I was looking for a boat for three years. In that time I sold some stuff to get enough money together to buy a boat and then out of the blue I saw the Freecycle ad for Sprite. So even if you do all your homework, visit all the yards and Marinas, make contact with boat owners in all the backwaters, you still need an element of luck to find your ideal boat.