I think it is easier than ever before. Platforms like BOS make it easy to find skiers, and if you show up as a good driver (which means being coach-able), consistently willing to help out, pay for gas, etc you’re sure to be welcomed back. Sure, it takes deep pockets to get on a premium spot on a private lake. It also takes persistence to get in with an established group, but my advice to the younger/college age skiers is never underestimate the value of being the first to volunteer to fix a buoy, move a lift, or clean the boat. Remember that time is often the biggest issue for whomever you ski with.
I love the numbers of young skiers we see at tournaments. One event this summer we had 5-6 B2 skiers all on the dock cheering each other on, lots of friendly banter about who was going to get what score. It was really great to see the younger groups start to gel and get that friendly competition that you see in the older divisions.
So while we have lots of challenges like the cost of equipment and access to premium sites, generally I think things are trending up.