Aye, there's the rub. Money is always an issue. Money may not determine the size and quality of the boat you set off in, as needs and mantenance skills play a big part here.
Yes, agreed most definitely... But what if money isn't an issue. I mean what if you can afford that brand spanking new Lagoon 400 with all the desirables from the options list that all the "cruising" magazines tell us we must have... And once you have it, you still have enough kitty left to cruise indefinitely and afford the upkeep (doing what you can yourself and getting someone else to do what you can't).
On that basis, are there any valid arguments to stick to something smaller and simpler? And are these arguments strong enough to ignore the old dictum I live by: "Happy wife, happy life".