Pam -- lease-a-bag sounds good to me. I know someone who even rented her wedding dress. Fortunately, I have 4 daughters, 1 daughter-in-law and 5 grand daughters who are now old enough that I can pass any bag mistakes on to them...and I already have.
Danielle -- You do carry a lot more stuff than I do.
I edited your list to reflect what I plan to carry around on our next trip: area-specific guidebook pages (probably ripped out), Moto X with translate app, SPF lip gloss, tissues, cough drops, antibacterial wipes (maybe), paperwork (like tickets), water bottle (maybe, we're old and lazy and prefer to stop in a cafe), camera (little Panasonic Lumix 20x zoom), room key.
All the stuff you are putting in that wallet will go in my moneybelt or neck wallet or divided between the two. My husband will carry his own. At best I will have some cash in the day bag. One of the good things about some of the Baggallinis is that they have a change purse with a lanyard that hooks onto it and onto the inside of the bigger bag. I've also threaded the lanyard through the elastic loop for the pen to keep the change purse more secure. And most have a zippered pocket inside the bag as well.
Putting all the important stuff in a wallet that isn't under my clothes is scary to me. There have been some posts here that illustrate how easy it is to pick a front pocket and even to get a moneybelt off of someone, but I feel very confident wearing a moneybelt.
This may be TMI, but I always wear industrial strength shapewear on the top, even in hot Tucson. I started doing it to smooth out the fat rolls, but when I fell in January, I realized that it may have been what kept me from cracking ribs. It also helps to improve my posture. When you wear that kind of garment, in spite of what you see on the (skinny) models, you are supposed to wear it under your panties.
I put the moneybelt between the shapewear and the panties (which are also of a shapewear type) in front. My stomach already sticks out, and I wear my tops over my skirt or pants, so I don't care if it adds a little bulk. I always know it's there. I haven't tried it in the back to see if I would feel confident with it there. In either case, the moneybelt is under two garments (skirt or pants and panties) and next to the shapewear, so it is not right next to my skin. Many others have commented that they wear moneybelts, so I just wanted to reinforce those comments.
There was thread recently about men who had had their wallets picked from their pockets. It made me wonder why they carried a wallet at all. To me, no matter where it is, it becomes an easily-pickable package that is all the more obvious because they had to take the whole thing out to get into it and anyone who was watching could see where it came from, what was in it and where it went back to. In addition, the extra thickness of the materials of a typical wallet make it that much more obvious in a pocket, and maybe easier to identify by feel if someone has their hand inside your bag.