1) I haven't had the Harbor Freight trailers long enough (or driven them far enough) to know about their longevity. I've taken one from Maryland to Louisiana twice, but the rest has been short 15 to 20 mile round trips to the local lake. And no, I haven't noticed any swaying.
Oh, I should mention about the AI sticking out beyond the back of the HF trailer: Technically, it's probably a wee bit too far to be 100% compliant with the DMV. I've considered having my fiancÃ©e weld a little extra section to the tongue, just to be safe.
2) With the AI, I do not back the trailer into the water. Instead, I assemble it under a tree (or any available shade) by using the Kayak Trax to wheel it away from the car and trailer that are usually parked on hot asphalt or dusty gravel lots. When I finish setting up, I roll it over to the ramp. The AI slips into the water, I tie it off, and I carry the Kayak Trax back to the car to lock everything up.
3) I can't afford new boats (I probably can't afford old ones either
), but I believe the new WR17s with jib kit and bilge pump are $8,995. The trailer's extra. I know of at least one dealer marking $1,000 off his in-stock inventory (this is the time of year many dealers are selling their demos, and rental places are replacing their inventories). And of course, there's the "previously owned" market.
On the other hand, a new AI retails for about a third the price of a new WR17. Even if you bought TWO, so a friend could sail with you, it'd still be cheaper (and you'd only need to buy one trailer).
I bought my AI used (from our Hobie Forum Classifieds), so I must credit the original owner with the pipe set-up on the trailer. He added the Yakima Hully Rollers and Saddle configuration, too. Boy, what an easy time I had taking the AI off and on the trailer. I bought the Kayak Trax, because I remembered what a BIG difference it made when I got the Cat Trax for my Hobie. It's SWEET not being "tethered" to where a trailer can go! ...and having the Kayak Trax made a big difference with the AI, too. Definitely worth the minor money for the major convenience.
But Kepra... These are the ramblings of a still somewhat novice sailor. In other words, my boat inventory and enthusiasm exceed my experience. But it doesn't take a decade of experience to figure this stuff out, and I'm glad if it was able to help. Your AI was a good first choice. Just remember: Two boats are always better than one; variety is the spice of life; and Excess is never enough
Fair winds and full sails,