Thanks for all the comments! Very helpful indeed!
I had two options:
1. Work out what REALLY needed to be done, then worry about the cost of doing what needed to be done to the engine.
2. Work out the worse case scenario of MIGHT need to be done, and attempt to come to terms with the costs involved.
I chose number two, as dealing with a smaller than expected amount of work/cost was always going to be easier to swallow than the other way round! It's just in order to really get my head around it, I needed to truly believe that the worse case scenario REALLY needed to be done - a bit of boaty method acting I suppose!
To my surprise, the idea of spending 3.5k on the boat to be able to keep her does two things. It proves that I really LOVE the boat and all that she has to offer, and that I am a total nutter with my head in an almighty bucket of sand... but then we're all boat owners, so I'm sure that doesn't come as any surprise!
Anyway, I think it's time for a bit of pragmatism, and Ed's ideas especially seem a perfect mix of cost effectiveness with a touch of going the extra mile for the sake of peace of mind. There's some things that really do NEED doing like the exhaust manifold/riser so they will of course be done. What's the thought on changing the following:
Starter and alternator. As mentioned, they're still the originals. Although not the biggest issue if they do break, but it will mean a call to ssea start if we are out, and likely a couple of precious boating weekends lost by the time we've sourced another and gotten around to fitting it. Plus, I assume if the starter does go, it'll be when you're just about to leave some far flung marina, meaning you have to pay for a tow back to your home port or pay to store the boat in the marina while you sort things out - either way incurring more expense.
Oil analysis - I can certainly see the benefits. Could the oil wizards glean anything from the 'absolute' data the first time around, or is it about establishing a 'baseline' and then making comparisons as oil changes go by? Or is it a bit of both? That said, either way, I guess a baseline will always be of value, and it's no good waiting for something to actually go wrong before establishing the baseline.
Carb rebuild - We had this done three years ago, but this season, when you accelerate hard from a slow speed, the engine bogs down. Accelerating gradually is fine. Is this something to do with the accelerator pump or something like that, and would a carb rebuild sort this? Also, in real terms how hard is this to do? I'm guessing it's got a lot og 'bits' but as long as you have a decent manual detailing the process and setup procedure, then with a bit of patience and fastidious following of the instructions, it can't be overly complex. My dad always talks about the carb on his old mini and how he always had that in bits. If he can do it...

Plus, although I understand how a carb works in principle, I am itching to see inside one to see how it actually does it's thing.
Compression test - I think I may start with this, as, although I doubt it, there's always a chance that the engine is running like a pig and I just haven't realised as I have nothing to compare to. Are the cheap compression test kits of any use, or are the readings they give too hit and miss / unreliable to be used? For a leakdown test, do you need an air line to pressurise the cylinder or is there another way of providing the air pressure (e.g. a tyre inflater with a check valve)?
Oil pump and petrol lift pump - what's the life expectancy of these? Are there any signs before they die?
Anything else that I've missed?
It's funny... I expect this winter is going to cost close to £1000 by the time we've done everything. I seem fine with that, but if I had to spend £1000 on my car, which I rely upon and use every day, I'd be livid! Do you know how many pairs of shoes £1000 can buy you!!!! At least two!
