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Like you, I have a large assortment of items I need to carry with me on a daily basis for work and the occasional play.
After several years of trial and error and looking at bags, I found these:

http://www.booqbags.com/index.html

I have the Python XM System with the 17" Powerbook sleeve. Everything fits perfectly in the bag, including laptop, AC adapter, assorted console cables to connect to my servers, file folders, webcam, you name it. The laptop sits a padded compartment separate from all the other items in the bag, and you can easily fit laptops up to the 17" widescreen ones (not using the powerbook sleeve, of course) in that compartment.
You can fit a PSP in the Logitech case in one of the side pockets.
The zippers have a special 'flap' over them that make them nearly waterproof, so you don't have to worry about water seeping into the bag thru the zippers. It's very nearly the perfect bag, IMHO.

I hope this helps you.

--
Evan

Mine of choice: Vyper XL

Simple; just something to hold and protect the unit. Somtimes, that's all I carry. If I need pockets for cables, charger, batteries, etc., then I use a briefcase that does NOT advertise "HEY, THERE'S A LAPTOP AND RELATED EXPESIVE STUFF IN HERE!!"

I always thought Booq made some fantastic laptop bags and accessories. Although it's predominantly aimed at Mac owners, the bags are obviously suited to other models as well. I have a Toshiba Portege which just loves the Booq bag it calls a cozy home.

Check them out at http://www.booqbags.com/

I have an old backpack I've been carrying around for about the last 10 years. I really hated giving it up for a laptop bag, but decided that I wasn't going to carry around an expensive Powerbook in a plain old backpack either (after doing this for a couple years with the Powerbook's predecessor).

I ended up getting one of these. It's padded and fits the laptop snugly, and hopefully gives it a bit of protection. At the same time it fits easily inside my regular backpack and the shoulder strap detaches when it's not needed. Cords and accessories go into the various compartments in the backpack itself and there's plenty of room left over for carrying books, my other electronic goodies (iPod, GBA, digital camera), and I've even gotten an Xbox in there with everything else before.

As an added bonus, it's much less obvious what's in it. That doesn't mean I leave it sitting around on the front seat of my car or anything, but every little bit helps I guess.

Mainly, it lets me transport my laptop relatively safely while still carrying everything around in my old JanSport. Can't beat that as far as I'm concerned.

I used to use a http://www.booqbags.com/ booqbag first generation BP3 model until it got pickpocketed in a Brussels café due to it having a flashy orange shell...I am curently using an Allyco Life backpack but rumour has it that the company is out of business so I have been eyeing a booqbag Boa.XM for my 14" iBook...I do a lot of traveling in Europe and I recommend getting something that has a minimum of zippered compartments, lockable, hidden zippers, waterproof, has stealth compartments (for hiding money) and is a solid black (or dark) color (I was told by Brussels police that colored packs = tourist = easy mark)...

2. Timbuk2 Detour. amazingly weather proof backpack, not nearly as narrow as the digital (the laptop goes in horizontally, not vertically) which is a bummer. also, the laptop doesn't hang like the digital so be careful setting the bag down. otherwise a superb product, supposedly totally weather proof (tho it hasn't taken the torrential rain test yet like my booq backpack did last year, and, btw, failed miserably!), and very well designed for accessories. also it's convertible between a backpack and an over the shoulder bag, unlike the digital which is purely a backpack.

note: i ride a motorcycle so i need extra heavy weather protection for my thinkpad. i've even crashed with the digital on my back and slid about 100 feet and the laptop, while a little banged up, still booted fine. (yes, if you were on the bay bridge at 10:30am or so last tuesday heading into SF, that was me sliding behind my ducati. one word: ALLCELPHONEUSINGCLUELESSSUVDRIVERSMUSTDIE)

In the past, I've used LOTS of bags; Spire makes some wonderful bags, and I used the heck out of an Endo with a previous employer.

I bought a Port bag for my TiBook when I actually cared about the "work appearance"; it's a sharp looking bag, and Port goes to great lengths with their air-suspension system. Heck, when I bought my first PowerBook, I bought the Apple-branded Port case to go with it!

I'd still recommend any of these cases, but most highly recommend Booq's bags.

Which Booq Bag do you have for your PowerBook -- the PowerSleeve? That looks like a nice compact bag, but does it have enough room in its pocket for a mouse & AC adapter?

Also Booq Bags. I've got the 12" for my PB and it's great in my shoulder bag or on its own!

(Ob:NotPaidAdvert)

One can try looking at booq, also. They make a nice (albeit pricy) laptop/notebook backpack. It's the only one I could find that would fit my Sony GRX570 and its huge footprint. (the 16.1" screen is nice, though)

I hump one of these around on campus and have been pretty pleased with it. Our campus has started going wireless, so occasionally I'll pack my laptop and my 8dB omni and sit ...where ever the heck I want. The antenna sticks out of the pack, so I look like an RTO.

Lots of interesting/ed looks.