I came to the conclusion a long time ago that once you move to the RV level, you have to tow something- whether it be a trailer or another vehicle behind a(n) MH. Which route you go depends on a gazillion factors and every situation is different. In the end, though, the final decision is yours, and yours alone. If you've done your "due diligence" and chosen wisely, you will be rewarded handsomely. However, I know people personally that have owned 4 or more different types of RV's during the (nearly) 15 years that I've owned my 2000 Jayco Eagle TT. For them, just enduring all the purchase investments, and depreciation losses on trade-in would have permitted them to stay in hotels!
We camped in our first RV, a Coleman Laramie pop-up, for 14 years. By then, our needs changed. My sons were grown and no longer wanted to camp with mom & dad and, of course, we were older and needed the convenience of a full bathroom and other amenities which the pop-up lacked. Being proactive, the DW and I had been attending an annual RV show for several years before making our purchase, looking for an RV that met or exceeded the requirements we established. In our case, a TT was the best choice.
We still attend the RV show every year, and when we leave, the DW and I look at each other and both agree there was nothing we saw there that excited us to the point where we would be willing to go into debt again.
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TV: 2009 GMC Sierra 2500HD | Crew Cab | Std. Box | 4WD | Duramax/Allison
RV: 2000 Jayco Eagle 266 | FBS | TT -- 1986 Coleman Laramie pop-up -- Still in the family!!!