I’m seeing lots of good stuff here from people who sound a bit more knowledgeable than me, so I won’t add more to the right truck \ right trailer combo question.
However since the OP didn’t say mention the fuel and did admit to being newbie … I’ll chime in with having had to learn some REALLY expensive lessons this last year with being my first winter with a diesel as my only transportation. First off I knew nothing about needing to change fuel filters at all, let alone how frequently. Secondly I had no clue how important choice of diesel vendor was. Thirdly I learned that “additives” are pretty much a requirement with diesel. I ended up spending more on repairs than I would have if I had just kept the small honda civic I sold. So I"m not steering you away from diesel at all, just be aware that you might have a learning curve with that if it’s your choice.