Ben, you're bag is just fine!
What you don't want to do is show up toting about six bags of unnecessary stuff with you. It sounds like you've got a good solid plan, go with it and when you finally get into your own truck you'll get the chance to go home and get some more of the stuff you would like to have with you on the road.
I've never heard the 24" requirement. Thats probably only so it will fit in a cabinet. I too was going to use a 30" duffel I already had, but discovered it was missing. I'm guessing my oldest daughter who stayed with me for a few weeks when she left her husband "borrowed" but she says she didn't. Anywho, I ordered a replacement but when it arrived.. great bag, but had been mislabeled by the manufacturer and was way too small. So my only option was to make a trip to the local walmart at the last minute and all they had in stock were HUGE suitcases or tiny travel cases. At least my weeks worth of clothes fits in it.. along with my unfolded sleeping bag lol. The smaller duffel, I'll just use as a shower/laundry bag. Yep, I'll be sleeping with a large suitcase lol.
You could use a couple garbage bags, "what" you pack in isn't important. The issue is like O.S. said, there's not enough room for you to bring everything onto your mentor's truck for 5-8 weeks.
A guiding thought: for your training ride, pack as light as possible. When you get your truck, and then get your first home time, it's moving day!
Old military trick on packing. Rather than fold things nice and neat, roll them tight. They won't wrinkle and you'll save a bunch of space.
I carried everything including my sleeping bag in my seabag. On my trainer's truck, my space was about 2 cubic feet. The little hole on top of the passenger side cabinets in a Cascadia. It was OK on a temporary basis. One reason I wouldn't want to be a trainer is because I don't want to do that again.
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I understand you would like as much space in your bunk as possible, the only reason I ask is I have one of those old on shoulder strap Army style canvas duffel bags and that is probably 30"+ tall (large enough that I can fit 1 weeks worth of clothes, Shoes, bathroom bag, sleeping bag and pillow inside) and I would prefer not to so buy a whole new bag if I can help it. so is the 24" recommendation a comfort thing or is it a "you're limited to a 24" duffel bag or you probably won't be getting on a truck"?
HOS:
Hours Of Service
HOS refers to the logbook hours of service regulations.