You really got a wide range of opinions! Some folks can take a 53 ft trailer anyplace they need.  Some need a great big engine with a seat sitting so low they can barely see over the steering wheel. Some can't imagine anything longer than a 22 ft trailer.  The one thing everyone seems to agree on is a 28-30 foot trailer is too much for this tractor.  You are going to have to decide what works best into your situation.

When Dad died we had a tandem with a 20 ft bed and 2 single axle straight trucks.  Dad thought the tandem was pretty big.  Son in law and I ended up with 3 tandems. We just couldn't convince ourselves to get semi's.  I was at an auction and in a fit of silliness bought a single axle tractor for a pretty good price.  I found a 22 ft Jet trailer in the AgTalk classifieds.  Great combination, loved driving it.  It would turn around in places the tandems wouldn't think about. Easier to drive than any of my straight trucks.  But after sitting and pondering we decided to go with full grown semi's.  We eventually replaced it and 3 tandems with 2 twin screw semi's.

For the most part I don't regret it.  Occasionally it would be nice to have a little straight truck around, but we held on to one tandem for a couple years before admitting we didn't use it enough to keep it.

I'm telling you all that to tell you this: If you think the truck you are looking at will do what you need and is a good one at a fair price, go for it. I would suggest a shorter trailer. I really liked my little Jet.  But if it doesn't work out you are not married to it. Upgrade as necessary.