Moondancer, you can see a picture of my Trailex double AI trailer here: http://www.hobiecat.com/forums/viewtopic.php?f=70&t=7276&start=435
Scroll down toward the bottom of that page. Personally, I'm not going to add a jack to mine--that will just add more weight, and to move your trailer w/ boat, you may
still need some kind of dolly. I guess you are thinking that at least you will not have to lift the tongue off the ground to the ball on your car. True. And, maybe with a jack, you can roll it into your garage or shelter a bit easier. Probably true.
The v-brace on the end of the tongue is 6" off the ground on my trailer when it is hooked up to my 4-Runner. It will not take a gouge out of my driveway. I'm not sure why yours did that--too low obviously. As you say, you can turn your ball hitch insert over to raise the tongue up. The v-brace can certainly be removed if you go for a jack.
Yes, Trailex tire holder is expensive (what isn't nowadays). Adding a tire holder + tire to your trailer will make it heavier--again. The tires are so small that I simply throw the spare in my 4-Runner.
My Trailex trailer with cradles installed
does not have a "raw edge" to scrape our AIs as they are launched/loaded. What are you using to support your TI on your trailer?
You can definitely put pictures (very helpful) into posts on this forum. Hobie does not "host" pictures; therefore, you must use some photo hosting service like Photobucket.com (free for a limited, but generous number). Then, get a "direct link" to your photo, paste that link into your Hobie forum post, and wrap it in Img code, e.g., [img]direct-link[/img]. I'm going to put some very specific instructions in the thread mentioned at the top of this post.