We started on the same search a year or two before I retired. While not the most important, budget was a consideration. My very old 4Runner needed to go. After lots of research, we decided that a truck and 5th/trailer was the right mix. Something we could leave in a campground, and then use the TV for getting around. Going up to a class A and towing a car was just too much for the budget. Going the towed route meant we didn't have to be too big, and had a better chance of finding more campsites.
Decided on an F-150 Ecoboost, with all the towing/payload options. It is a daily driver, so didn't want to be saddled with too much truck. Finally settled on a Jayco 26.5 RLS Fifth wheel. It just made all the numbers for the truck to carry/pull it. Took many trips to all three coasts, most being 3-4 weeks, in that combination for the last 4 years. We found the 30' fifth was overall a great match for the needs of 2 adults and 2 50-60 lb dogs. Not so much if we tried to add in my daughter/granddaughter for short 3 day trips - it was pretty crowded. Some of state parks were unable to accommodate the length IF we didn't make reservations well in advance, but overall it wasn't much of a limitation. We did tend to stay at private campgrounds on the longer trips, as full hookups were easier to get.
A roof tear resulted in the walls of the fifth delaminating, and insurance totaled it. All small fifths have gained weight since we bought ours, so no replacement that the truck could handle. The big lesson - buy more truck than you think you need! Some of the newer fifths that are a foot or two longer, with more slides, would have been fantastic. We are now waiting on delivery of a 32 ft. Travel Trailer. Might have to be slightly more selective on campsite selection, especially with how "backable" the access to the site is. But I don't anticipate that it will be much of an issue. New one has main living double slides, which will make it feel huge.
For longer trips (a month, etc.) pay attention to basic daily needs storage - cookware, clothing, cleaning, etc. What you can get by with for a week is much less than for a month. We found, with that size, that a month was about enough for us - then we wanted to get back to a "real" house. After that, it started to feel limiting for daily living. That's where the bigger fifths, Class A's, etc. start to come into play.
2012 F150 Eco, 4x4, SCrew, Max Tow, HD Payload
2017 Grand Design Imagine 2670MK