Annual resort park pass. Is it worth it?

I'm gonna throw you another curve ball. You say you are new to camping, and it shows. Nothing wrong with being new, but I think you may need some more tutoring on what to expect. You seem to be talking about buying a pick up/camper combo, and camping for weeks and months at a time, with a 2 year old. Might be OK for short term trips, but it's awful tight for anything longer than a week. You will be much better off in a travel trailer for extended periods. Also, from bitter experience, the wifi you want to depend on for your lively hood while on the road may not be as reliable as you need it to be. We have been in many campgrounds and "RV resorts" that advertise wifi, but what they have is very limited, spotty, and many times broken to the point you can't do much more than send or get a couple of emails. At any rate, welcome to the road whatever you decide to try.