Living quarters toyhauler would be your best bet honestly if you want to bring both. Then just park them in a straight line.
If you want a bumper pull you will probably need a 32-36' long camper. i would look at something like a 23pack15 by forest river. This SHOULD give you your length needed.
If you want a 5th wheel, then look at a 255rr. This is the one we are considering. It's a 1/2 ton towable 5th wheel, with a dry weight of only 6800lbs. Well within the limits of a 3/4 ton diesel. and only 30' long!
I would just look at the combined weights of both of your machines loaded up (full tanks of gas, cargo boxes etc), and make sure it fits into the max capacity of the camper. The 255rr can carry over 4500lbs..
Would need more specs on your tow vehicle (crew cab/ext cab/4wd/2wd/long bed/short that kind of stuff)
and your street glide (motor size, Length & weight specs)
then the weight and length of your 2 seater commander (figure 10' long and about ~1500lbs with a full tank of fuel)
i would recommend a 5th wheel slider hitch for the bed, if you go that route. With your bike being 8' long and the commander being just under 10' long, you'll want a trailer with a minimal of 20' cargo space so that way you have space between the back door and the front of the camper. I would actually look for one with 22' living/cargo area myself just because i'm a bigger guy and can't fit into too many tight places lol