Thanks a lot for all your replies! That helps a lot.
I actually towed a travel trailers 4 times so far: one time with Ford 250 + some 23 ft RV of 3000lb dry weight, and 3 times with a Cadillac Escalade + 22 ft Airstream (dry weight 3900lb and GVWR 5000lb). Comparing all these trips, of course the Ford 250 + 3000lb trailer was the easiest drive simply because it was such a powerful TV dealing with a relatively small trailer. The Cadillac Escalade + Airstream was not as a good driving experience, but Airstream itself is really a good camper, and I enjoyed the camping part so much and those trips convinced me about owning an RV.
However, even with Airstream, I observed the owner dealing with all kinds of small to medium issues (loose screws, faulty furnace etc) all the time, and the Airstream dealer was not helping much in those cases (The Airstream trailer belongs to one of my closest friends, so I know lots of those live examples). I expect that for all travel trailers, owner needs to fix some issues, but with better quality and customer service, the burden is much less. That's why I ended up order Oliver instead of the Airstream I loved, for its simplicity, quality and good customer service. Still kinda of nervous on if I can handle the fixes and other things later, but I guess I have to learn and adapt as probably Oliver is the one with least concerns.
As of towing a trailer, I have to admit I still need lots of practices 🙂
Thanks a lot for all your support! Looking forward to my journey together with all of you!