10w 40 full synthetic should be fine, I'm pretty sure there isn't a crush washer on the drain plug, I've always just tightened to spec ( 7.1ft/lb's IIRC) and never had an issue. Just check the condition of the o-ring on both the drain plug and oil filter cover New o-rings are usually not needed, there are no gaskets. Both DOT 3 or 4 are fine for brakes.
I carry this in the black cordura multi pocketed tool kit:
10mm x 1/4" socket
12, 13,14, 15, 18mm x 3/8" sockets
5 and 6mm Allen bolt sockets
Full set of 1.5-10mm Allen Wrenches
Multi bit screwdriver
Duct tape on 18mm socket
Lock nut/spoke wrench
8-10mm open ended wrench
Various cotter and widgeon pins
missing chain link
spark plug wrench
4" extension bar
double headed short handle 3/8" and 1/4" ratchet
Box of spare allen and hex bolts
inner tube patch kit
In another tool tube I carry:
2 tire irons
2 motion pro tire spoons
aluminum spray tube of Windex
bicycle air pump (not pictured, but in tool tube)
Above the headlight on the cowling I have mounted a small bag that carries two replacement tubes and a tire gauge.
I have never been at a loss for tools.