I've owned a Z110-BT since 2010 (w/ firmware upgrades through the years), and am ready to pull the trigger on an upgrade to NEX-8100.  I've used an iPod 5th generation with this unit with no issues the entire time.

I just want to confirm what I'm inferring from other posts on this forum.

If I connect this iPod to the NEX-8100 (via USB-2, because I will connect my iPhone to USB-1 for Carplay), will it lose "resume" capability every time I turn off the car?  If so, this is probably a show-stopper.  I very much enjoy having my entire music collection available, but not if it "restarts" every time I start the car.  The other kicker here is that there really isn't a good replacement available on the market.  Apple stopped making the iPod classic, touch is overkill for this purpose & 16Gb on a nano isn't near enough.

If this is a known limitation with a 5th gen iPod, could others provide their solutions to this problem as well? (other than just buy a used 7th gen on ebay, craig's list, etc..)

If any of you are successfully using a 5th gen iPod connected to USB-2 on any NEX, I would love to hear that as well.

Thanks.

You are correct.  I've experienced this with both of my 5th gen iPod's (one 60, one 80) and the 8100NEX.  

Being that the pioneer unit doesn't support playlists on USB or SD storage devices, the only alternative for you might be to play your music from your iPhone via car play.  My solution (which you've stated you don't like) was to purchase a used 7th gen iPod classic.  (My fallback to that would have been to get a refurbished ipod touch 64GB 4th gen.)