Does either option include a lesson on the operation
and maintenance of the machine, including demonstration?
(with Sears, I doubt it). You obviously have a vehicle
to transport the chipper, and I'm sure they will load
it up for you...but will you be able to unload it when
you get it home? Either way, make sure you get all of
the paperwork that is supposed to come with it, (manual,
warrantees, etc.). Whichever method you choose, make
sure you check to see if there is any oil in the engine
before trying to start it.

Suggest you determine which manufacturer makes the chipper you might purchase and check those pros and cons. Look for a couple of local chipper dealers, make visits and ask for a demo to start and run. The much older chipper from Sears that I had was nearly impossible to start. The recently purchased 5+ hp Briggs generator requires a good pull so try it. Since Sears probably does not service at the place where you will purchase check that aspect. When I had a mower repaired, it was sent 200 miles away for diagnosis. It was too expensive to repair -- so I let them keep it. Example, Echo has an electric start chipper. Visit sears.com site and find the Craftsman 305cc Chipper Shredder and read the comments from purchasers. Home Depot sells a 305cc yard machine, rated as a 2 of 5 by a buyer and I think quite a bit cheaper than Sears.