Hey Felstead; I am a player exactly like you. I can't speak with real authority on the headphone issues you're worried about but I just wanted to chime in on your VHT candidate. I have the VHT 12/20 head running thru Celes V-30 (4). It is an AMAZING amp. I never see/read word one on any forum about VHT but I can say, from experience, this thing can keep up and shine alongside my buddies expensive Boogies and Egnaters. I'm with you on the Blackstar - not a fan. If I had any advice for you I would ask if you've noticed not all tube amps "take a pedal" the same way. If you use pedals you should try them with the amp (if U can) before U buy it (?) Another rig I have/play is a 6watt Fender Champ running thru a 4x12 cab with just an old BOSS DS-1 and it's great and plenty loud for a garage jam. On the rare occasion I want headphones I use my little Yamaha THR amp. I know this isn't real "help", I just wanted to cast my favor for VHT. Good luck, every amp candidate you mentioned are really good amps.