Learned a few things when updating my Pineapple MK5. (After you restore your pineapple back to pre-brick condition:)
1. RTFM
2. Have a fresh SD card inserted before doing the update to 1.0.1 (refer to 1)
NOTE: The Hak5 crew provided a way to format your SD without having to use another computer. Goto Resources->USB Info
3. Know your DIP Switch (refer to 1)
4. Don't blow away the SD that came with your purchase. (Don't be cheap, buy more!)
BTW: To answer my own question. It doesn't take that long to complete the update. After Unbricking (AU) and Before Setup (BS) it was 5 minutes or less from start, download, install, reboot.