We were in the same position two years ago. My wife and I started with our honda civic and a tent. Many fond memories taking sponge bathes with a bucket of hot water. After our three kids came along we ventured into RVing with a no thrills no slide 27' TT. Since it was our first I didn't want to have to worry about slides leaking, not deploying, etc. We loved that trailer taking it on trips to Yellowstone, Black Hills, many trips to Colorado, Civil war sites, etc. On our last trip in it with our older kids, we found ourselves tripping over each other...we had outgrown it. We purchased a Rockwood 8281ws FW and have loved it. We didn't know anything about RVing when we started and as we camped made notes about what we liked and didn't like and continue to do so. We have had no regrets about upgrading and will do again when the kids are out of the house
. We like to camp in state parks and national forest sites so will keep our trailers under 32' so we can get into the places we like to camp. Sometimes it is a challenge with that size! We also like having a large grey tank so I'm not having to empty it often. Good luck in your upgrade!!
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