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I have noticed that a good chunk of songs, particularly older ones, use whole-song fade outs as outros to end the song. By "fade out" I am not talking about playing a final note and having that fade (like this), I am talking about the whole track fading like in this song.

Whole songs fading out make it more awkward for DJs (if they do actual mixing) to transition, so I'm curious why they would choose to have them.

I know there are stylistic elements to having this (which don't appeal to me), but are there any technical reasons for this technique?

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    Sometimes songs fade out in order to deny listeners of the resolution that comes with hearing the ending. If there's no ending note/chord then listeners will have the song stuck in their heads longer, artificially improving the songs odds of catching on and becoming popular. The same is true for songs that don't end on the tonic pitch, also denying listeners the closure of a real ending. – RedCaio Jun 8 '16 at 2:42
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There is no one technical reason for this, but there are some things that deal with the technology/requirements of the time when whole song fade outs were more popular.

Quoting from this NPR article on the subject:

"I'm pretty sure fade outs did not occur during the days when 78s were used ... since in those days music was recorded directly to disc. Once studios started using magnetic tape for their masters (early-mid 1950s), it would have been possible to do the fade out in post production mixing sessions." - Tom Larson

"Most time(s) it was because the arranger didn't have an ending, or to shorten the arrangement for air play. Remember, back then singles wouldn't be played if they were longer than 3 minutes." - Al Schmitt

"The fade-out became a way to end the record in a manner that perhaps suggested there was more to come." - Dan Daley

"I believe that one of the advantages of fade-outs was that we could repeat the hooks and drive that message home." - Elliot Mazer

"The fade happened because we had to give the DJ a cue that the record was ending, so he could talk over that and segue into the next record" - Ron Albert

Then again, these are only some possible reasons. The true reason in many cases could be a stylistic, "this sounds good to me" or "I can't think of a good ending" as well.

For more detail, check out Billboard's post on the subject.

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    Note the distinction between the historical definition of "DJ" meaning a person who makes announcements during radio broadcasts, and the questioner's refering to a "DJ" as a live performance remix artist or beat maker. From the sources quoted above, fade-outs seem to have been created for the benefit and convenience of radio announcers up through about the 1970s. – user546 Aug 24 '15 at 2:23
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Agree with Zach. In addition, some songs were played in concert Grateful Dead style with the song followed by an extended instrumental jam. In the record studio, the jam would be faded out just before a clam was played or the jam was running out of steam.

When the intro is faded in, this is for the same reasons only in reverse order.

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