I did just what you're talking about, ten years ago-- two adults (a couple), and a two-room tent-- we used one room for cooking/dressing, the other acting as the bedroom. We were also there in winter (Jan, Feb, March). It was wonderful! I think you'll love it.
Here are some things that really made the stay nice that come to mind-- and please excuse me if I'm saying stuff that's obvious to you, as a seasoned camper. I'll skip the basics and try to think about the "glamping" elements (love that term!). I've also done lots of camping/hiking/roughing it...and it was so fun to have such a posh setup at Disney!
Tent:
Two-room is great! Mine was tall enough to easily stand up straight and walk around in, which to me (also having done lots of camping in small tents) made a HUGE difference. So much nicer to get dressed, cook, just move around when you're not hunched over / banging your head. Also the door was really big, not requiring crawling in and out --also nice on the back!
I liked having the kitchen inside the main tent, and not in a screen tent, mainly because it's often quite cold out at night that time of year. It'll be cold cooking breakfast and dinner (and sometimes chilly at lunch) in a screen tent. I used one of the rooms in my main tent, which had plenty of ventilation anyway between the vented roof and large windows. That way, I could put on my nice heater and be all toasty while cooking. Also no worries about scurrying back and forth through the wet if it's raining.
Bedding:
Instead of an air mattress, I brought a king-size memory foam topper (a 4" thick one), which filled the "bedroom" nicely. Bulkier to pack than an air mattress, but imho waaaaaay more comfy. Tho it was a just little thin for side sleeping-- you might be able to improve on this idea. A thought-- I've bought memory foam mattresses (the bed version, not a "topper") from Sam's Club online-- inexpensive, often with free shipping. They arrive with all the air sucked out-- quite compact, at least on the trip down. You open the container, and it "inflates" over the course of a few hours. If you can find the room for it, I'd far recommend memory foam solutions over an air mattress (having slept on both long term). This might be the biggest "glamping" tip I've got-- you wouldn't believe how awesome it is to camp and be in a truly comfy bed every night! (A very weird feeling after all my time camping atop rocks, bumps, etc!)
Electricity
One of the most ridiculous glamping things at Disney is that you have electrical outlets just a few feet away, at every tent site! Bring one power strip for each "room" so you can set stuff up once and leave it. Super convenient, but I was a little concerned about safety in the rain/wet. I'd recommend getting an outdoor circuit breaker/fuse (GFCI) to protect you from short circuits in the rain...also waterproof plug covers are good for peace of mind (
example). I made sure that all my cords went UPhill on their way into the tent so that rain couldn't run down them towards a plug. You can use clothespins, binder clips, or clip-style clamps to secure your cords in "uphill formation" at the door to your tent(s): Clip one binder clip just inside the door, down low, to hold the cord in position where you want the tent door to close around it (but choose a position as high off the ground as possible-- definitely not ON the ground). Then clip a second binder clip a foot or so off the ground, to hoist the cords uphill, just inside the door. Use zip ties (re-positionable!) or twistees or string or chewing gum or what have you to attach the cords to the clips. I hope that makes sense!
Heat
I researched and found that
a Vornado heater like this one was a great fit for the tent. It is super-quiet, and gently uses a vortex fan to fill the whole space with heat. It turns off if tipped over, and the whole thing stays completely cool no matter the setting. Perfect. This thing was AWESOME. OK, maybe this one is the best glamping tip! Toasty warmness plus memory foam...STYLIN'! In the two-room tent, I put it on the "bedroom" side of the door between the rooms, but it could easily heat both rooms by opening the door between rooms a bit, or turning it around to blow into the kitchen room while cooking. Was plenty for the space. Also great for drying laundry / towels / bathing suits that you've got hanging in the tent!
Work Surfaces
I brought two folding tables (
example), and floor protectors (
example) to protect the tent floor from the table legs. They come in all different lengths and foldability (some fold in half for packing), so you can get whatever you think would be a good fit. But having two or more is really helpful, so you're not at a loss for workspace.
Lighting
Clip lights (wired) on the edge of your work tables are really handy.
Cooking
A double-burner hotplate (electric cooktop) with automatic safety shutoff (if left on) was great (
example). It lets you boil pasta or make rice while cooking stew/sauce etc.
Silicone potholders - bring a pair for picking things up, but also a couple that you can leave on the table surface, for when you're serving or just need to get something off the burner right away. Silicone because they don't get damp/moldy if it's rainy, and easily washable, quick dry.
Use a clip to pin up a small garbage bag, to a table leg by your cutting board, for example.
Foodstuffs
I used a dehydrator so that I could bring homemade stews along with me. Just add water and simmer for a bit! It's "fast food" that doesn't need refrigeration.
Random stuff:
Zip ties - repositionable (I mean the ones that you can tighten but also loosen again-- waaaaay more useful)
bungee cords
clothesline, clothespins setup (or twisted bungee clothesline that you tuck corners of clothes into without needing clothespins) for inside AND outside the tent
plastic clips / clamps (or binder clips, cheap tho they rust eventually)
That's what came to mind immediately...Any questions, please ask! I hope you have a great time.