je & after
you are making generalities that do not fit everyone.
I bought my first sailboat last spring. I did not take any asa classes nor any other sailing classes. I had about 10 days on the water on other peoples sailboats over my lifetime. I did own a 26' power boat for 15 years.
I'm doing very well sailing my Endeavour 42. At times I'm not happy with some aspects of the boat but ALL boats are a compromise and I quickly remind myself why I accepted the compromises I did. I researched sailboats for 2 years before buying this one. I have been putting in a lot of work on repairs and upgrades. There are no major issues with my boat, only routine stuff that needs tending to and some upgrades in electronics, like a radar & chartplotter.
We'll be heading out for long term livaboard cruising next year.
Do you really need to stick with such a short mast? That will limit your selection, probably to ketch rigged boats only.
Keep in mind that you will find 5 times as many things to attend to as you think at the time of purchase. Do not discount the effort to do something as simple as changing out old hoses. I have not had to put in tons of money but I'm doing all the work myself. I have a lot of hours into simple stuff like the hoses. Save at least $30,000 of that money for the refit/upgrades. Plus taxes, survey, insurance, etc. It does add up!
Last thing...do not be in a hurry. Take your time and do the research on different boats, rigs, equipment, and go look at a lot of boats.