Distance is about 12' or so, so not very far. Plan is to come into one of those wall boxes, 90 down into the crawlspace with rigid 4" ductwork and tape it together all the way to the cinder block foundation where I will slope it down gradually. Punch a hole through the block, toss the cap on the outside and tape it all together.
Wether or not to insulate it I'm still uncertain. It's a cool crawlspace and the basement isn't heated although they are connected to each other and it's rather moist in the crawlspace. The dirt is packed but always damp and there is batts of fiberglass above in the floor joists but the foundation blocks themselves are only insulated, poorly, by some of that crappy paper-ish spray foam stuff that came before the polyurethane stuff. Would have to scrape it all off to insulate it with rigid styrofoam and I just haven't yet but I probably should eventually.