Helpful posts from Bob and KRviator, I reckon. Personally, I don't find it too onerous and offer my own implementation as a suggestion as to how to handle the Sunday pie-run requirements.
I have a lightweight laptop wallet with a few zip compartments. The wallet lives in my "big" flight bag. Within the wallet - in various compartments - live my iPAD, a couple of VNC and ERC(L) charts, printouts of a couple of ERSA local aerodrome diagrams, licence/logbook, spare specs, ASIC, phone, money wallet, keys and emergency Minties. The idea is that I can quickly grab the laptop wallet and go for the Sunday jaunt in the puddle-jumper, with minimum overhead.
Within the puddle-jumper, I keep all the legally required documents (MR, flight manual etc) plus an operations log in which all flight times, fuel in/out etc are noted.
A lot of this stuff is common sense and only a little bit of attention to regulatory nuances gets you happily into the air for that $100 pie.