What a great thread. I feel reluctant to add my ramblings to it but here goes.
Disclosure I am 62 years old retired and have been sailing dinghies since I was 15. At the age of 39 I bought a 22 foot trailor sailor and sailed it around the West coast of Scotland and down the Adriatic the following year. At 43 I was lucky enough to be in a position to take an extended sabbatical and cruised the North Atlantic and Caribbean for 7 years on a 38 foot steel boat costing £15,000 [It was a lucky find and a good buy] and a annual kitty of £5,000. I am just about to set off again on my forever boat.
Over the years I met many people on a huge variety of boats, nearly everybody was having a good time. The size of the boat did not matter.
But I did meet a few who were flying home, leaving their shattered dreams behind them and the boat for sale. Their boats were often large, full of gadgets and their owners relied on shore based maintenance services. Sometimes they had had a big fright, some realised they just had bought too much boat and some found they could not cope with that peculiar Caribbean concept often called "Island time".
My first two cruising boats taught me to be self reliant, to avoid having anything essential that I could not maintain myself, that repair manuals, tools and basic materials like sailcloth, aluminum sheet, gasket material and threaded rod were more important than perfect brightwork, a teak deck and a perfect holly splined cabin sole.
I devoured stories of cruisng boats from Swallows and Amazons to the Hiscocks. They were amongst the first cruising couples, their first offshore trip taking them to the Azores and back before setting of on 17 years of "Wandering" and two circumnavigations.
The Hiscocks did not go to sea to experience hair-raising adventures. All of their voyages were carefully planned and flawlessly executed, with few surprises, and in the proper way for a middle-aged British couple seeking only personal tranquillity and the freedom of long ocean passages. In their quiet and competent way, without the fanfare of a Chichester or a Blyth, they came to epitomize, perhaps more than any yachtsmen in British history, the proper seagoing citizen.
Eric Hiscock disapproved of EPIRBS SSB etc saying if you choose to go offshore you should not rely on people coming to rescue at the risk of their lives if something goes wrong. I admire his resolve but did have an EPIRB and SSB and a liferaft on my 7 year wanderings around the Atlantic basin. I never needed them but my mother was glad I had them.
For my part I was glad I had a steel boat on two occasions the first when a whale played chicken with us for 4 hours, the second when we hit something big at night. While I did not have insurance I did have oversize ground tackle and a 100 lb storm anchor. I only deployed it once and it took me 7 hours of back breaking labour to recover it. I finally got around to fixing the anchor windlass after that.
If I could afford a brand new properly painted steel boat I would have another tin job with an Amel Super Maramu a close second [only 2 mil]. But a tough "old shoe" in fibreglass is my choice for my forever boat. I will make sure I can get to all the fittings and that nothing is hidden behind a fibreglass panel needing a sawsall to gain access.
I used a sextant in the past but GPS is great, If the boat comes with an electronic chart device I will keep it but paper charts are essential IMHO and I like to keep a running plot of our position on an hourly basis.
One thing that I added in my second years cruising was a powerfull hand held spotlight for the odd night time encounter with a strange boat. I will have another and make sure it is driven directly off 12 volts with a back up battery job.
Wherever possible everything will run off 12 volts and will be chosen for low current drain. Efficient refrigeration, LED lights etc. I shall have enough solar and maybe a little Honda 2 kw genny.
In the end of the day seamanship matters more than the boat and a positive mental attitude overcomes many shortcomings. I loved the story of the £200 millionaire as the sunset is the same regardless of the boat.