If you want to have someone else do it, you can open a private store at some place like zazzle.com or cafepress.com and upload photos that meet certain graphics requirements and pay them for the shirt and printing.
You can also look for t-shirt places around your area that will do it in the phone book or online yellow pages.
You can also go to an office supply store or place like walmart that sells special printable iron-ons or t-shirt transfers to print them yourself. You can get cheap blank t-shirts at craft stores like Michael's or probably Joann's.
Quite a few jackets have a removable water proof liner. My mesh jacket does and it works fine keeping me dry. Doesn't do anything to help my legs though.
Some mesh jackets have a couple of liners, one waterproof and one insulated. The Tour Master Intake Air Series 2 is one. A jacket like that will give you a pretty large range of wet/dry and well as temperatures.