I for one have never found shifting to be at all traumatic. The automatic transmission on these machines are nice… but if you want to talk about simple technology of yesteryear…dang!To follow up on the Honda statements..... yes the bikes of "yester-year" (Late 1990's thru mid 2000) were some of the most reliable bikes ever produced - IMHO. BUT, to get an "automatic" transmission in a Honda, you now have a hydro matic type transmission just like our daily drivers!! On that note..... I'd much rather replace a $75-100 Belt (or even have a little clutch work done), then have a $2500-3000 automatic transmission bill!!! This is the way the dealer I went to summed it up for me when I was looking to buy new. I was looking at a brand new Honda 650 & Polaris 800 side by side on the showroom floor. (Note: That Dealer only sold Honda & Polaris) I asked about reliability.... and he said he see's both of them come back for work. It's all in the maintenance/up keep!! But if you go Honda..... and want 110% reliability. Go with a 2000'ish Rancher 350 ES 4X4, true work horse... but don't expect a smooth ride or a performance machine.
If using it for lite "plowing, dragging and trailer pulling" as the OP's requested in original post..... If your looking for a Polaris, I'd say you couldn't go wrong "Used 500"!! As 6hp is a lot when we are talking 35-36hp for the 500 to start out with. And in our area Ridinagain is dead on..... should be able to find a "Good and Clean" 2005+ model machine for $3000-4500 easy. Don't settle on the first one as, but rather look for a lightly used one with lower hours & miles and you'll be very happy!!!
Good Luck in your search!
Simple is good and depending on the job simple old tech is sometimes best.