Our first TT was a 16 footer. It was a 1991 Prowler and it was my wife and I and two pug dogs, occasionally. It was cramped but, we had some amazing trips in that trailer. That was in the early - mid 1990s. Would I want to do a 16 footer now? No way. I would if I had to but, given a choice, no way. We sold a 28 foot class A motorhome a few weeks ago. That's the size range I really like. Our travel trailer is 27 feet and it's the perfect size for what we like. It's not crowded feeling, especially with the slide. If you're rained in you can relax and enjoy the day. The old 16 foot Prowler weight 3600 dry. This 27 with slide weights 5500 dry. Not that much more for more than twice the square footage with the slide out. If we had gone back to a small trailer I totally would regret it.
But, it's important to know what you plan to do. We like to go to the beach and hang out for a week. Or maybe the mountains for a few days. We don't go out to the boonies and dry camp. For that maybe a small camper would be the way to go. Essentially we have a vacation home at wherever we want to be. That always includes full hookups, cable TV and wireless internet. Roughing it means that the nearest restaurant is more than 10 minutes away.