1/ How much cold hard cash can you front up with????
I decided, in my typical under-realistic dreamer way, to go against all my well thought out plans and instead bought a boat I fell in love with, that wasn't on my radar, and was bigger than I'd decided I could afford. I subscribe to the 10% rule: 10% deposit and borrow the rest!

Well, not really but I did borrow to buy the boat.
I have no assets and basically no debt. I just spend what I earn. People die. I will die. I'm living as fully as possible until I'm wrenched from this wonderful world. I had 2 kids I couldn't afford by the age of 23. I did three degrees that took thousands of hours and dollars for the joy and the journey (and as an investment, but I would have been better off if I'd been a plumber, I reckon). I took a year off five years ago and backpacking for a year with my wife, blowing $70K. I'm broke but I'm living as best I can.
2/ How much cold hard cash can you continue to fork out along the way?????
When I was looking at buying a boat some very experienced people on this forum gave great advice about how much it costs to run a boat, right down to categorised dollars and cents. One person just exclaimed, "Everything I earn". I was horrified, but in the end that's been my experience over the first two years. I've repowered her, rerigged her, and am on the long journey of replacing pretty much every pipe, bolt, screw, cable, chain and piece of cloth around her 30-year old bones.
3/ How much cold hard cash can you afford to drop at the end of the day??????
I can't - that's why I can't sell her!

I have to keep taking wonderful, 'free' holidays to make all the expenses earn their keep. Maybe one day I'll sell and move on from sailing or (more likely) move up to a bigger boat I also won't be able to afford.
But that's just me.
FWIW I would have been better off waiting, saving, and buying a 60 or 70K boat instead of a 23K neglected boat. But I didn't have the enough knowledge in this area at the time. At the time, I would never have made that decision because that would have been 'too much money'!!!