Here's my thinking...
I need peace of mind when buying. You can't know everything about a boat, not even with a thorough survey by the most competent surveyor. There's always something about to break down, always something hidden trying to take your boat to Nature's original state. A better quality boat that is well maintained will increase the odds of not experiencing too much of that.
We're going to look at it this weekend. Right now, the boat is on the hard. We may have a motivated seller. But in the end, it's are we willing to commit to the cost of ownership? that will determine if we will become boat owners. This will not become an emotional decision.
You are the only ones who have to love it, and you should base your spending on your needs and desires, this is not an investment, it is a luxury. It is something you do not because you have to, like food, and so forth, but it is something you do because you love doing it. Spend wisely, use your head, but also use your heart. If you look at the boat and you love it and it is worth to you what you have to pay to get it, then buy it. It will be your responsibility, and your money that has to go to keeping it the way you like it. A good survey is much needed and if you see that the survey reveals things that would make the boat worth less, then show that to the seller, most times they will accept that and either repair it, or reduce the price, often by a lot.
Ten years ago I was looking at a boat, it was more than I could afford, but it caught my eye, and even though the owner was asking $65,000.00 I offered $29,500.00 not because I was trying to lowball him, but because that was all of my budget, plus a little. I made an offer in earnest through a broker, I put up the entire amount in escrow with the broker. He went to the seller and the offer was rejected, but then a survey done by the broker turned up some issues. It was six months later, but I got the boat at $20,000.00 and spent another $18,000.00 on it in repairs and replacing things that were needed. I sailed it for three years, and sold it for $29,000.00. Most people would say I lost money, I would say I gained something money could not buy, the experiences of not only sailing, but also working on the boat. I was happy, and I was the only one I had to please.