I picked up this handy bag from Amazon and it's served me well but I'm needing a bit more room without moving up to "backpack size".
It's just a cheap imported bag but it has held up good to daily use except for the stitching on the handle came out and it fell off. 
I keep my iPad and other essentials in it but I would like to be able to keep my carry pistol in it when needed and it gets too cramped when I try to do this.
Anybody know of any under $50 bags that might serve my purposes? (iPad+Glock 19+wallet and checkbooks+Mora Companion+keys+etc....)
Thanks.
(Standard iPad in an Otterbox measures about 8" X 11")

I have picked up some old laptop bags and what not here and there.  Ask around, some folks might just be getting ready to throw them out.

I want a shoulder strap on my stuff, do you just carry that like a brief case or do you use a strap or what?

I also have backpacks and what not as well.  Heck, been known to use an old hard briefcase I added a shoulder strap onto as well.

I guess I am not picky.  I like bags and cases and what not.

Sometimes the answer is right in front of me.....
I forgot that I had a range bag in the closet that I rarely use. Actually, I bought it to use for an EDC bag several years ago and I thought it was too big so I did not use it for that.
Works perfect. Everything fits and it has a ton of little pockets and lashing loops. MORA Companion in a kydex sheath fits great crossways in the top slot.
....and I didn't have to spend a dime.

Cactus Jack Tactical Sling Bag