Help me fill my Overland Travel tool kit
Wow, provocative question. Provocative in the sense that the ultimate toolkit is dependent upon the overall condition, age, serviceability and level of alteration of the target vehicle as well as anticipated service required by the payload ie. camping systems/gear/bikes/yaks/etc. Let's not forget the other half of the equation, the skills, abilities, experience and motivation level of the user or users. No two rigs, trips or "overlanders" are the same, so there is essentially no correct answer to the OP's question.
A high functioning toolkit is very unique to each of us. There is no way to definitively predict what will go wrong, when and how many times. Access to replacement parts, number of vehicles traveling, temperature, etc. etc. etc. all factor in to what tools to take so the subject is best approached from a philosophical standpoint.
Know and understand your rig's tendencies and fastener types
Know your own mechanical repair capabilities
Anticipate conditions (roadside, Wal-Mart parking lot, dust, mud)
Predict chances of access to carried spares or auto parts store
Decide how much space in cubic displacement and weight you want to concede to tool transport
It's easy for a skilled mechanic to have the ability for major overhauls, it's unlikely such a task will take place on a journey. Just because you can rebuild a transfer case, and hard fourwheeling can result in a destroyed a TC, doesn't mean you will overhaul yours trailside. Bringing too many specialty tools doesn't make sense for a lot of us. This community is famous for overcamping, over preparation and overloading, your toolkit is a compromise to weight, space and capability. You can't predict every situation. Some of our passionate members will tell you they will not leave the curb without X, Y or Z. For them that's great, for others maybe not. Go back to a philosophy that makes sense for you and your mode of transportation.
I will add a couple of things I have found through experience and if it meshes with your toolkit philosophy, great...if it doesn't, no sweat off my brow. I wish you the best of luck arriving at YOUR answer to this question that has no universal answer.
-Commercial tool sets, of reputable manufacturer are good starting points
--(depending on size) They usually should be pared down to eliminate the seldom and/or never used items
--The injection molded plastic organizer they come in is an inefficient and un-tailorable storage solution, pitch it
-Explore soft tool bags for storage: sturdy, reconfigurable and don't waste space with unused volume
-Tool rolls are nice for wrench organization, not so much for other tools (pockets are too randomly sized)
-Rails are a must for socket storage and organization
-Harbor Freight is a sensible source for certain tools
--Not a good source for sockets or wrenches that require good fit or use in high torque (will break or strip fasteners)
--Handle the tool before purchasing it, if you question it's ability or quality on the rack, it will be questionable on the trail
--Hammers and prybars from HF are in my kit
-Have dedicated tools for your shop and a dedicated set for your rig
--This ensures you have your tools on the trail and didn't forget to put it back
--Try to use your rig toolset in your driveway when wrenching on the rig, you will learn what you really use and what you don't
-Don't "over think" your tools, you don't have the space or GVW to take everything with you for every conceivable event.