I dry hop 8-10 oz pellets (no bag) 2x in my ss brewtech chronical for 10 gallon batches of 7%+abv NEIPAs. I'll add first addition on day 7 after yeast pitch. On day 11, I drop as much as I can. I had the same problem of hops getting stuck at the bottom and contacted ss brewtech. They suggested I move the drop valve back and forth continuously until the hops push through. I will also put a pound or 2 of CO2 on the fermenter to help push the hops out. It's a pain in the arse, but it will work. Then I add the 2nd dry hop addition on the same day. Usually by day 14 I have reached my FG, I push some of the remaining hops out (dip tube does not reach the botton of the conical) and then do a closed transfer with 1-2lbs CO2. I use a large and small bouncer filter in line during transfer to kegs. With a little getting used to, that process works pretty well. Since adopting this process, my NEIPAs have been light, brite, fresh and stable.
FYI, prior to transfer I fill my kegs with sanitized water to the top and push out with CO2 to minimize O2 contact. I forgot, I also I will cold crash down to 40* for about 24 hours on 1-2 lbs CO2 prior to transfer.