What's your bike frame? Based on my experience, the biggest problem would be the frame can accommodate fatter tires or not...

I agree, upgrading the wheels needs a lot of $$$, I suggest not to do that unless you exactly know what you need and what you want.

...because oiling the chain will usually oil the dérailleur sufficiently. I think what you mean is how to clean your rear dérailleur : bicycles.stackexchange.com/questions/18521/…

A possible duplicate question: bicycles.stackexchange.com/questions/20378/…

I'm not sure why do want to edit your own routes, can you elaborate more?

Get a touring wheelset since they are designed for fully loaded bicycles. For example, Mavic A719. For more consideration, to get a quality wheelset you definitely should talk to a bike mechanic. Purchasing bike parts online is risky since you cannot inspect the quality of the parts and many things can go wrong if you don't have knowledge about bike mechanics.

@Jasper. I agree, you even need to measure the sizes of the components to fit your body sizes: stem length, handlebar length, saddle width, crankarm length, etc. Wrong measurements mean you are screwed.

It's good that friction-facts has done a lot of research but data should be easy to access and widely available. It's funny that the reports should be purchased ! (friction-facts.com/test-results/individual-reports). More importantly, the data should be translated to writing that general people can understand. Without proper education/explanation, data is just data.