I can't answer the HNL question specifically (will they take the bags that early), but you shouldn't have a problem checking bags at 2 different periods. I've done it once earlier this year, using the kiosk both times. The 2nd time I went to the airport, the kiosk knew that I'd already checked 2 bags, and asked me if I wanted to check more.

If your PNR is eligible for 6 for free, you should be able to do 2 and then 4 later.