Awesome read. BTW, both UPS and USPS (don't know about FedEx, etc) will pickup packages on demand. Of course, if you live in an apartment, this does mean you have to be home at the time.
Not sure whether it's changed, but USPS pickup was only free a few years ago when you shipped Priority or higher.
I'm surprised how much time was spent writing addresses by hand. Paypal Multi-Order Shipping and cheap adhesive shipping labels, which can be found on eBay, take a lot of pain out of that process.