+1 on Wheeldock. My Chieftain is always in one when I'm not riding. A GREAT chock. The added flexibility of being able to move it quickly to a trailer is pretty special. I could not recommend it more. best of luck.
I recently heard someone talking about using trailers, and he suggested renting, since most people will only use trailers two or three times per year, tops. However, this is aside from the current topic. I just thought I'd throw it out there.
IMHO. If you have room to store it buy one. That way you can put all of your mounts and tie downs in place and leave them there. If you rent a trailer three or four times, you will likely have spent as much as a small trailer costs. And I think from looking at things cost aside, the Wheel Dock looks like the best for the Indian.
I have the better one that harbor freight sells, yes I do have to get it over the hump to get the back part to lock the wheel in place, but it holds it up on it's own. I run soft ties up inside the fairing, don't ask me where as I don't really know how to describe the place right now. I did have to cut the front part of stand down as it would have hit the front fender as it's rather tall. I have a Stealth trailer in all aluminum with torsion axles, it's the only way to tow. I have my stands bolted to the floor with 3/4 in bolts with hole drilled in center and tapped for 1/2 bolt so I can remove the stand easily if I want to. Saw that on someones website when researching stands. I also saw one that would let the suspension still move, but I was a little skeptical about it keeping the bike secure. I do have 3 lengths of E-track running on each side and down the middle to attach bikes to usually running tiedown to ring. Don't know if I like using that system or not, it's worked so far. Worried a good jolt could pull the pin out, but I have drilling all kinds of holes in the trailer floor as well and I am not exactly sure they would hold either. Well that's my two cents.