Wolfepack, you've got a pretty good and comprehensive plan.  Here's my 2 cents:  Some real-life first-aid training or at least read a good mannual and watch the Tactical Medical Solutions vids on U-Tube.  More bandaging material, especially 2 "Izzy" battle dressings.  A small survival/first-aid mannual.   A good all-purpose sheath knife.   My favorite for a GHB is the Gerber LMF II.   A Katadyn water purifier bottle and a Ti cup fitted on.  Even better would be a General Ecology XL pump water purifier.  A couple of water filled, wide mouth Nagalene bottles.  Not just pepper spray, but a medium sized can of bear repellant pepper spray in a nylon belt holster.   As to a walking stick, I suggest an oak Canemasters crook neck cane, fitted with a convertible rubber/metal point tip (available from Leigh Valley or Treeline) along with a basic video on its use.  Canemasters will install the tip, for a fee, if you send it to them with your order.   Finally, as to cash, is it $200 or more?  I'm not sure I understood your post. $1000, broken up would be best.   P.S. Forget swimming! In case you ignore this advice, add 2 airline type inflatable vests.  One for you and one for your pack.   Best of luck.  
Agree on additional medical supplies and training.  My two first-aid kits (one to use/leave at the office, one to take with me) both come with first-aid manuals.  My deck of survival cards, while sounding cheezy, has some good survival related info on them.  A bigger first-aid book for the office is a good idea.  Though at the rate the suggestions for first-aid supplies for the office are piling up, I might as well open my own trauma ward.
The walking stick is something I am still investigating.  Will look at Canemaster you suggested.
As to cash, sorry if I was not clear.  I have a total of $200 split into two $100 groups stored in different places in my GHB.  My GHB is only intended to get me home.  I have a bigger and better equipped BOB at home.  $1000 in cash would be great, but I certainly can't afford to have that amount of cash just sitting idle at work for the next 10 years.  Personally I think the chances of my GHB being stolen while it is stored at work are much higher than any emergency big enough that I would need the GHB.  Just my own personal view though.  Now if you happen to have an extra $1000 you could lend me, lets talk!