I can relate to all boats....older, well used, show pieces, and beaters. I purchased my first new boat, a Pro Line 22 WAC back in 1998. Great boat and fished saltwater for several years. All other boats (except for my current new one) were 10-30 years old, but well maintained.
Owned 10-15 sailboats between 1980 and 2013 of all types...Cat Rigged Ketch, Sloops, dinghies, and one racing boat. Lenghts of 8'-35'. Lived on the 35' custom built sloop that I purchased from an aeronautical engineer that hand built it from keel to stepping the mast. Teak decks, varnished spars, Volvo diesel, just a very classic and beautiful sailboat. Spent many of days varnishing and keeping her mint!
My well used 13' whaler was fun all of the time! Jump in and GO! Kept in water behind my sailboat, and was always ready to go. Bottom cleaned, and maintained mechanically with safety equipment and running gear. Not the prettiest whaler, but in good shape.
I would say I had the most enjoyment with the well used, but well kept boats, sail and power. I never allow my stuff to be junk/beater level....I am always looking to improve.
Now, at retirement I have a new '23 boat and a new '23 truck. Saved for these toys for several years. I wanted new as my last truck was 20 years old and was eventually going to need reopairs that I did not want to tackle. My new boat...I wanted a side console boat that was beamier, with under deck fuel tank, rod storage, and capable of a larger (60hp) motor.
Yes, I find myself wanting to keep my boats, trucks, toys, etc in MINT condition for as long as I can. But, they'll eventually get scratched, dented, dinged, etc. I'll have to learn to live with that, and that will be difficult with my OCD!!! But, they'll be my dings and dents...with memories to go along each one!
At my older age of 60, I want to enjoy things more and not worry so much about being in MINT condition. I'll leave the MINT stuff to classic cars and show boats. For me, now, practical, simple, and clean is preferred.
Basically, get what you want and enjoy it to the fullest...life is short!