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1 bag for all my gear

OP, how important is it that you're able to get all of your stuff loaded in on one trip? If you have to do it all at once then is it possible to find some kind of case for your amp head that you could bungee onto your cart with your Aggie cab? Theoretically you may be able to find a bag that attaches to your cart which could keep your stand safe.

It depends on how far you want to go with this. I live in NYC so I'm often using public transportation. Compactness is very important to me! Just because of the nature of the game, my set up is very heavy. Its good that I'm a big dude, because this stuff is still a pain to go up flights of stairs.

Typical gig load out:
-Mono M80 (holds my bass, big flap on the bottom holds sheet music, paper, pens, CDs, business cards, markers, tape)
-Mono Guitar Tick (holds my collapsing stand, cables, DI, extension cord, power strip, strings and trimmer winder, more tape, tool kit)
-Maxpedition backpack. This one. It has molly attachment loops and the attachment straps so I can secure my pedal board on the outside of my bag. Inside of the bag usually has water, phone charger, and a light change of clothes as well as any costume stuff. For a long time I had a markbass LMII in there, but I sold it. Soon I'll stick an Aguilar TH500 in there.
-Folding Handtruck from magnacart. Aguilar S210 is bungeed on.

Nice setup! I'm working on something similar with a double bass gig bag, PedalTrain PT2 is soft case, Bergantino B Amp in an old Timbuk2 messenger bag and will (hopefully) soon have a lightweight Bergantino cab (still looking for a lightweight cart, any suggestions?).