TG. The best dio's tell a simple tale but should direct the eye to the main item of interest - the vehicle. The secondary vehicle/figures need to be the things that are telling the story being delivered. I'll give you some advice based on my past experiences which I hope will be of use to you.
I would do a smaller base for a first go. Just big enough to have the despatch rider on his bike alongside the JT. The figure you have is ideal for a commander talking to the rider. A simple but very effective set piece.
Why do it this way? Large bases needs lots to fill the gaps other wise they look just like a couple of models on a board. 'Fillers" are easy, water filled arty craters, discarded track links, old boxes, jerry cans, etc - but it is easy to overdo it and easier still to under do it, especially during your first attempts (trust me on this - been there, done that, seen that ). Also larger boards require a lot of static grass, clumps of long grass, trees, etc, and getting that to look right also takes practice.
Two large models on a board can look crowded and splits the view of the beholder. More than two vehicles (even as small as motor bikes) can also make the layout crowded. You want them to look at your fanastic JT, not 'look a few models together and oh, look one is a tank (destroyer)' . The bike emphasises the size of the JT nicely in what you are proposing and is great, but the second bike begs the viewer to ask 'why 2 bikes at the same place?' I hope all I've said makes sense.
Take a look around some of the stuff in the dio forum, ask those guys for some tips, and I'm sure you will be happy with the result.
Oh yeah, AND THE jAGDTIGER LOOKS GREAT!