There are some comfort issues involved here, too. Pickups are easier to drive, and they come with as many comfort features (e.g., extended cabs, bells and whistles, etc.) as you want and can afford.

You can also put your pickup money into purchasing extra power, which makes them more versatile, too. Most box trucks putter along by comparison, although there are exceptions to that rule, of course, if you’re willing to spend enough.

Then there’s the price factor. Unless you’re buying a monster truck with a huge trailer for your landscaping business, you’ll usually be on the hook for a lot less money.

Now let’s talk about the downsides of a truck/trailer setup. Backing up is one-you’ll likely need to bone up on your use of mirrors, but even if you do your visibility will be limited.

You may also need to do some extra work when it comes to preparing your job-related routes. It’s difficult to make tight turns with a truck/trailer combination, so you need to prepare in advance for any unexpected surprises. Also, you’ll need to reevaluate your parking spaces at different jobs, as it takes extra length to accommodate the truck/trailer pairing.

Finally, there’s the two-vehicle nuisance, i.e., you’ll have to register both the truck and the trailer, and your insurance setup will have to account for both vehicles as well. You’ll have to factor the extra annual expense in your budget as well, not to mention the time it takes to keep both vehicles up to date in that regard.