Either way will work but the more you are on the road the first year, the better chance of finding a campground you will like. Also, take drives and tour campgrounds ahead of time to see if you will like them before booking.
Our first 11 years were in pop ups. We parked it at home and camped anywhere from 4-12 trips a year, our year being May to Oct. the kids were little and had some great trips, the kids started camping at young ages, 1 year, 5 months and the youngest camped at 4 weeks old.
When the kids got busy with sports etc our camping dropped off as baseball and softball went into the summer and soccer started before the fall. It was at this time we went seasonal. We found a campground that we liked that we had never been just over an hour from home. Bought a 30 foot trailer and after 1 year loved it so much we upgraded to a park model 12 wide. I know many don't like seasonal but it worked for us, our second home. Campground had 400 sites, kids had a second group of friends, we had more friends, some we still camp with. Things that we did not do or have at home: golf cart, campfires, 4 pool complex, huge breakfasts at the site (50 people once), bands, dj's, bingo, volleyball, and on and on. The kids could not wait to get up there. Sometimes we would go fot a day or one night depending on activities but we were basically up there some part of every weekend, May to Oct. for 11 years. The memories are great.
Now for the last 4 years, we tow the 35 foot trailer and get out 14-16 weekends a season. Love the towing and the wife and I do the setup pretty quick so all is good. The youngest is 19 and still joins us and our oldest tent camps with his wife and joins us from time to time. We love traveling and all, just love camping. We keep our options open as health might force me to go back to being seasonal but for now, all is good.
As you can see, many things will work and once you start, you will see what works best for you. One advantage I have is the trailer is in the yard, plugged in and ready to go all season. Happy camping.
ME '63, DW 64, (DS 89 tents on his own, DD 92 not so much), DS 95
2013 Premier Bullet 31 BHPR 2014 F350 Crew Cab 6.2L 3.73