since I just spent a boatload of $$$ on my new Mac, I'm essentially broke. My kids will be eating cat food for the next month or so
You obviously have your priorities well in order.
I would have made the same choices myself, had I had kids.
[doublepost=1532182705][/doublepost]One alternative to a messenger bag is a small backpack. I've been looking at the
Samsonite Paraglider Light model series, because it's available in stores in my city; I don't have to order it over the interwebs and then wait for days or weeks for it to arrive, I can just go out and buy it.
Paraglider Light backpack is available in two major sizes, one larger with two major compartments, and a smaller one with just one major compartment.
Both bags are well padded from impacts from every direction, and have a very clean, clutter-free, waterproofed synthetic exterior without any abundance of straps or other details as seen on many backpacks. One might almost be tempted to call them "Apple-ish" in appearance; especially the white color pack...
Zippers are also sealed and waterproofed, and major compartment zippers can be locked together with a padlock. There's a comfy carrying handle at the top, an extendable flexible mesh water bottle holder in a side pocket, a springy address label holder that can be pulled out on top of the medium-sized rear pocket (which cannot be locked), and a small, quite shallow "hidden" pocket (also unlockable) on the side of the pack which rests against the user's back when worn. The shoulder straps are well padded and can be clicked together across the chest to improve weight distribution and comfort.
Both size backpacks have a padded laptop (or tablet) pocket inside the large compartment, unfortunately only the larger model bag has a velcro strap to secure the contents of the pocket - a bit of an oversight there, so one best keep it upright when on the move... The larger pack also has a smaller pocket suitable for a tablet alongside the laptop pocket, while the smaller pack features a phone pocket (again, without velcro strap), two pen holders and a mouse pocket complete with a velcro closing flap inside the main compartment. The large pack moves these pockets and holders to the smaller of the two rear compartments, which means that if you're out and about and want to secure your all your stuff you'll need two padlocks; one for each major compartment... A slight first world problem, one might say.
Anyway, as this is Samsonite, it means these packs are a bit pricey, but on the other hand the quality also seems very high indeed, (as you would expect, as Samsonite makes travelling luggage which needs to stand up to abuse without falling apart), with strong materials and very well made seams. Every compartment is well put together, there's no visible and unsightly fringes of material anywhere and it all feels very sturdy. The one issue that I can see is that due to the rainproofed nature of the bag the materials used probably don't breathe at all, so if there's any moisture inside for whatever reason (like a damp piece of clothing you stuffed in there) it won't escape naturally. These packs need to be opened up to dry out.
In closing: I'm actually very tempted, especially for the smaller bag which seems quite handy. It can also double as a travelling backpack, which is two birds with one stone! (If one is into bird massacring, that is...)
