I’ve had lots of success with mega hoppy beers, and I don’t pressure transfer.
The keys things are:
Keep the fermenter sealed up with an airlock when fermenting. Don’t open it to check what is going on.
When you dry hop, you can just crack the lid open, throw in the hops and then close it again.
For mega hoppy beers I also dry hop in the keg. Putting them in a hop sock works fine, but I’ve also built a filter for the dip tube so I can dry hop loose in the keg.
If you’re cold crashing the fermenter then I highly recommend using a Mylar balloon partially filled with CO2 in place of the airlock.
Before transferring to the keg, purge it with CO2 - and by that I mean fill it with water/starsan and then push that out with CO2.
When you come to transfer, you can fill through the liquid out post of the keg if you want to, but I’ve found that unnecessary.
I have a tap at the bottom of my fermenter, and just run a length of tubing from that into the bottom of the keg, and I temporarily cover the keg lid opening around the tubing with some foil.
The CO2 doesn’t all immediately escape - there’s plenty enough to cover the beer while transferring, and obviously it is getting pushed out continuously by the rising liquid level. Just don’t stand around too long - the moment you’re done transferring get that lid on and some CO2 in the keg.
If you can fill the keg to the brim then that’s best, you’ll just need to blow a little out or your beer will struggle to carbonate.