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a good rule of thumb - to not use enhanced mode while achievement-hunting. some achievements are not obtainable with that option on. not sure about "40 Year Old Virgin" tho, but quite possibly enhanced mode prevents getting it. not 100% sure
How you get from point A to B to C and so on the quickest relies on which task you choose to do first and what routes you take.
Good luck.
for instance, there's a big thursday skip where u get arrested and sent over to the cop shop right after picking up napalm, where one can hand in their parking fine to the dropbox without having to exit the maze of the burning factory, while also skipping over the travel you have to make from factory to police station