I’ll add my two cents as a “lazy entitled young person”.
I grew up in a tiny town where board was no more than $250/mo at decent facilities (no professional barns in the area, but private ones). My parents couldn’t afford to pay for lessons for me (not that there were any English trainers within a 2-3 hr radius anyways) so I taught myself as much as I possibly could and spent countless hours at the barn cleaning stalls, learning and riding my free lease OTTB, trying my very very best to be a sponge.
In college, obviously still broke, I worked summers at a dude ranch - 10hr days, 6 days a week for $200/wk plus housing and meals. During the school year I was a full time student, a collegiate athlete, worked a part time job AND STILL chose to be a part time WS 30 minutes away where I got ONE 30 minute lesson on a dead broke school horse at a mediocre barn for every 15 hours of labor I logged. I knew I was getting taken advantage of and I did it anyways because it was the only opportunity I had to learn and be around horses. I woke up at 7:00 every morning and went to sleep at 11pm and every 15 minutes of my day was planned out, just to keep on top of it all.
After I graduated, I wanted to take a gap year and just be a working student with an eventing trainer to really learn more and improve under an actual trainer (instead of just watching hours of clinics on youtube). And yet, being a largely self-taught rider without any real equestrian resume to speak of that would show off how qualified I was to ride their horses, the only one who considered me was a woman who didn’t pay anything and offered one stall of free board (to bring a horse that I obviously couldn’t afford to buy, let alone tack or vet bills) and promised exactly zero ride time. So I didn’t do it. Not because I was lazy, or felt entitled to ride time or because I didn’t think the lady knew anything and I didn’t respect her experience and knowledge, but because I simply couldn’t afford to and if ANYTHING had gone wrong, I would be royally f*&#^d. No medical insurance, no money to move if she had been a horrendous person. Even as it were, I would have had no money to pay for groceries, let alone gas and car insurance and my parent’s sure as hell weren’t going to subsidize my “hobby year”.
So now I’m 26 and have a 9-5. I still can’t afford my own horse, but can afford a cheap partial lease on a fresh OTTB 45 miles away (yes–I literally pay to train someone else’s horse for them), and I still work several hours a week at the barn (on top of my full time job) for a weekly lesson. But!! I have health insurance in case I get bucked off, an emergency fund for when Dobbin decides to injure himself, a retirement fund, and can pay my bills and provide for my family. So I guess there’s that.
OP’s situation sounds wonderful, and if I were in a different stage of life I’d jump at the chance to learn so much, and I’m not even a dressage rider. But at the end of the day most WS jobs are a very high risk, low reward gig and more and more it seems like the ends simply don’t justify the means. I’ve been given more free rides as a paying client who just tries to be helpful and a general pleasure to have in the barn, than I’ve ever gotten as a WS.
But idk, I guess I’m young and dumb and don’t care enough about horses enough because if I did, I’d just work harder.