This is a tough question for someone else to answer. One man's crazy is an others genius :B.
While the amounts of initial outlay may be similar. I think that's the only comparison. With a new truck, you end up with Well a new truck and keep an almost new trailer. The truck would be under warranty and you should know the condition/history of your trailer. With a 10+ year old class A, you will be buying someone else's problems and without warranty or fore knowledge of it's shall we say quirks. That's not to say there aren't any decent RVs in that age range, but I have been around RV's my entire life and my family and I have owned many and every one I've ever seen has its own quirks/issues.
You indicate you are pretty handy and could handle most DIY projects, but is that how you want to spend your time? Some people enjoy working on them as much or more than camping in them.
A couple of things to think about.
Your current trailer is only a couple of years old. Did you buy it new? If so, you know how its been cared for. You know its good points and bad. Do you have any experience with older RVs? Do you know what to look for to cull the "good" from the "bad"?
Many 10+ year old RVs have low mileage, but that's not necessarily a good thing. Vehicles that sit for 11 months out of the year with no or very intermittent use don't age well.
Most 10+ year old RVs have been stored outside and uncovered most/all of their life and most have not received proper maintenance when it comes to roof and window sealants. Most have been exposed to some leak damage somewhere.
If you don't like your trailer or want the class A experience, that could be a determining factor. There are pros and cons to travel trailer/fifth wheel vs motor home.
You don't indicate any parameters other than cost, but at 60K you are in the territory of new class C or newer low end class A units.