Is regear needed on a 4cyl on 285s?

Will eventually regear sometime in the future but I am curious of how bad the truck will struggle for the time being with a 4cyl engine on 285s.

From where I am from, 40 mph is usually the top speed we hit and I do go uphill quite frequently.

 

285 is the width and there are many different tires sizes, sidewall height and diameter that use that width.
16”? 17?

 

You could go 33" on 255 pizza cutter tires and save yourself a lot of headaches, cutting, regearing etc.....

 

Considering plenty of people re-gear with 33's with V6s, I would imagine the 4 cyl would struggle. I have a V6 with 33's and it works fine for me. Sometimes it stays on high revs and will take some time to shift up when I'm going 70-80mph but it eventually shifts. I do have the typical symptom with stock gears and bigger tires but I don't think my V6 suffers from my 33's enough to warrant a re-gear but I've also heard some people with 35's with stock gears and pulls trailers with no problem.

It's one of those YMMV kind of things.