Go on a weekday and practice you trailer unloading and loading, with your girl or anyone you with be with often also. 90% of the boating mistakes I saw were made at the boat ramp. Learn how to tie off too. Clean it after every use. Change the fluids often, and keep the tank full to reduce air in the tank.
I used Facebook marketplace to buy and sell some motorcycles recently. It’s probably not much better than craigslist, but at least for most potential buyers you can view their Facebook profile to get some idea if they are legit.
For a coffee solution your best bet might be to get with the owner of Champs and see if they are interested in doing something better than the little self serve coffee brew and gas station pastries. I’m sure that they have seen the demand last year with people coming in every week. Maybe they would be willing to provide something more.