I guess it depends on what your idea of more comfortable is. I owned a Silverado and it didn't ride as good as my Tacoma or the other Tacomas I've been in. We drove my buddies Tacoma from Washington D.C. to Fort Collins straight through only stopping to eat, use the bathrooms and one 15min nap and it was as comfortable as I would expect to be on such a trip. Personally, I prefer my trucks to feel more like trucks and less like cars. I don't buy my truck for ultra plush road trip comfort nor do I buy it for Pruis-like fuel economy. If I can get decent in both of those categories while getting ultra reliable w/top-of-class off-road capability all while providing the best resale available.... I'm good. I don't expect it to ride like a Caddy nor would I want that. Somewhere around 20mpg works just fine for my needs. I don't have any horse trailers to haul so I'm good with my truck for my needs.
As doe interior... are you trying to so that a 2008 Silverado has superior interior quality because I have a hard time believing that's what you're saying. I'm not saying the Tacoma is wrapped in leather and the finest materials possible but it is put together well and I don't think my Silverado beat it in any way as far as interior goes other than room. It should also be noted that my Silverado was an SS so it was pretty much the flagship model as far as Chevy trucks of that vintage go. Sticker price was MUCH higher than that of my Tacoma new and current used values aren't even close.
I haven't had any troubles with my engine (only 40k miles so I wouldn't expect to either) but a few things are a PITA when working on them for sure. I had to pull my supercharger to do a plug change but that's not something everyone goes through and I knew what I was getting into when I bought it so no big deal. Common things are a breeze though. Oil changes take me about 10min total and I don't need any tools to do it either. The Silverado had it's own PITA things to work on though & this goes for every vehicle I've ever owned so it's tough to fault any one of them as each one has something that's a nightmare.