Here is my current combo. A 4x6 tilt tongue utility trailer with 15" side rails and a PV flat top TD.
As for your plans, you may want to look at having a bottom to the TD and then have the skids attached to that. Rather than have the TD bolt to the trailer, you'd be probably better off to use 'J' hooks of sometype. That way you won't have to lay on the ground to loosen the bolts throught the trailer bed. You could do it standing up. On the same layout where the hooks would be secured to the TD, why not look at adding stands to hold the TD up. That way you can lift 1 corner at a time and actually lift the TD off the trailer. And if you are innovative enough, get a crank style stand. You rotate the stand, crank to load it, then go around and do the same. Then crank enough to actually lift it off the trailer bed. (IIRC there is something like that on a Aussie fiberglass camper recently shown in this forum.) If the stands had the capability to have different ends on it, you can go tri-pod or casters. Casters for moving it around the garage, tri-pod for longer storing. (IIRC same as the Assie site.)
Lastly, do a search here about trailer TDs, slide-ins, etc. There is some discussion on it previously.