Don't take this the wrong way or anything, but it seems a little unusual to me for someone interested in "retrocomputing" to be frightened of learning gruesome technical details about how computers "in general" work. If you look at the fanbase of other old-tyme-y computers you'll find that almost every individual in those communities is "frighteningly technical" and not afraid to get their hands dirty in anything that enables them to get more out of their old machines.

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Such is the difference of the Macintosh experience... don't forget that tinkering was strictly discouraged in the early days!

But getting back to the original topic... it most surely is possible, but as others have said it will require a journey into the unknown. Contiki OS would seem the logical place to start, since it already has a proof-of-concept email client that sort-of works on a 64K Apple II. The first hurdle would be that, as far as I know, no one's yet ported Contiki to 68K.

Edit: never mind, I just reread the original post and realized we're talking about using an OS X machine to do the heavy work.