Are we going to run into a lot of campgrounds in California we cannot camp in?
No, you are not going to run into a
lot of campgrounds in California that you cannot get a 33 foot trailer into. However, it depends on your driving and backing skills. Some folks cannot park an RV in an area the size of Walmart and others can park one easily in a small space. The 33 feet is total length and some of that, at least 10 feet, is behind the rear axle. If you keep the wheels on the pavement and let the rear hang over the pavement end where there are no rocks, posts or trees the site becomes much bigger without any effort. Don't let the campground sites stop you from getting what you want. If you ever run into a campground you want to camp at that is too small for your trailer, a few miles away will be another campground or RV park that can accommodate the trailer. This campground size thing is overblown and nowhere near the issue some make of it. In every campground in California I have camped since 1987 with an RV, if you can get it into the site, it is not too big. The numbers published for sites are guides not limits.
Never go smaller than what you will need three RV's into the future. If you go smaller you will be looking for bigger next year and the depreciation on the existing unit and new unit cost will not be insignificant. Save the money now and get what you want. Many experienced RVers will tell you that longer trailers are easier to back up than shorter ones. A shorter trailer is shorter; not necessarily easier to back up.
Another vote for a one ton truck to tow 33 feet. Be comfortable towing, not at the ragged edge of a tow rating for a marginal tow vehicle. If you go crew cab on a truck you will be 56-58 feet long on the highway. You do need to plan your lane changes and turns. Practice in a big parking lot if you think you might be nervous about backing and be sure you know how to use the mirrors. Otherwise, go for it!