Trailer Sailer Place is an excellent resource but also check out this Facebook group for a more visual experience
www.facebook.com/groups/5540365149308152A Trailer Sailer is an excellent starting point into sailing. Easy to rig and handle, inexpensive, fun and portable and a better platform to learn sailing being more tender than a keelboat so less subtle and more of an immediate need to get things done right, but without the fear of capsize. The thing about keelboats is they cost money to have them sit unattended at a marina in a pen or on a ball somewhere whereas a TS can sit on your driveway costing literally nothing whilst you aren't using it. As a 40 yo, unless you have retired through a win fall or similar, you'll be working M-F and only get a few weeks off per year.
Lots of great boats to choose from, from as small as 16 or 18 feet, up to 30 feet. Welcome to sailing. Not a bad idea to do a Day skippers course.
DM