Hola- I have a cash kitty of about $80K to purchase a liveaboard 30-42 footer. I'm very handy & can make my money go far. My question: Is it more prudent to buy a newer, more expensive boat that needs less initial work, or an older one that I can update more extensively from the start?
First off, I think you should really look at how you intend to live and what your needs are. We aren't liveaboards, but we have recently upgraded from a 30ft boat to a 42 ft boat and they are worlds apart. If you truly can live on a 30ft boat (many do) you will be way better off in monthly costs for moorage, initial purchase costs, etc. When we were looking for our current boat, we noticed a huge difference in the liveability between 36 or 37 ft and 40-42 ft. For us it translated into more aisle in the salon that we deemed important because of the two boater-collies we have.
That said, I think you are right in the ball park to get a decent boat you can enjoy for that amount of money.
As far as budget and your kitty, consider this: ANY boat you buy will need some sort of investment. Even a brand new boat will come with costs for you to outfit it (with the exception of a very few companies that deliver a complete boat including cutlery and towels.) We made a list of everything that would be a requirement for us, a good to have, a plus if we had it, etc and what the associated costs would be for each boat to have what we wanted. EG one of our requirements was some sort of diesel heat. A good to have would be a hydronic heater, as that would give us hot water without running a genset. We determined costs for what we could install those systems for, me being somewhat handy. As we shopped for boats, as we saw a boat lacking our required things or needed things we added that cost to what our eventual cost to buy and outfit that boat would be (along with whatever taxes and etc would need to be figured in.)
To get to the nuts and bolts, we had a kitty of just over $84K for our boat. We purchased it for 56K, and after taxes and etc for the purchase, had 18K left for the repairs, upgrades, outfitting we required, needed, or wanted.
We've done all the work ourselves and shopped for deals on all our purchases of equipment and supplies. We've used all of our 18K and more, and still have several major projects to do - one is a requirement (recoring a soft aft cabin top) and the other a want - a robust solar installation. We've had several projects come up that we haven't known of, as with anything, and religiously followed best practices in the selection and installation of equipment. One example is the hot water heater basically made it halfway through our 3 day delivery trip. It was never installed properly, with an AC plug underneath it...the project included completely rewiring that AC run from the breaker to a new outlet installed just for the heater, a new heater, relocation of the heater to make better use of space in the engine room, clean, degrease, paint everything along the way....you get the idea. This will be typical of most every project you touch on your new boat.
We spent a decent amount of our kitty on some electronic upgrades to the boat, to the tune of probably $2900. We put in an AIS transceiver, a Nemo gateway, a fusion radio with amplifier and 6 speakers. We also have a 10 sensor Aqualarm system we're putting in (engine, high water, and fire alarms) None of this was required to have the boat safe or functional, but we felt strongly it would make it more enjoyable and comfortable for us.
We'll be able to do both of our unfinished projects, we'll tackle one this summer and one next spring, using funds we're setting aside for boat maintenance, but that's how quickly you'll eat up an $80K kitty.
FWIW, our boat came to us 98% functional, with needs to replace some batteries and exhaust elbows. We knew about the soft aft cabin top, and had a list of other things for us to do. It came with all the docking, mooring, and anchoring gear we will need as well as dishes, cutlery, filters and oil, original equipment manuals, etc. We picked it up and spent 3 nights on it taking it home, so it definitely wasn't a "project boat" but it wasn't a 100%er either.