The bigger the old boat the more room you'll have, the bigger the head-aches you'll have, the higher the cost(s) for parts and maintenance.
Speaking from experience, started with a 10ft boat up to a 45' boat back to 32' now, but you know the saying "a boat owner always wants a bigger boat and their current one is always for sale because of that"

As a matter of fact mine is for sale for a steal.