Hare scrambles races in Southwestern PA can be a very good learning tool and quite the challenge. They have a great mix of tight technical terrain, they mix in some more open faster sections here and there. The terrain in any one of the races of the various hare scramble race series in the area can be fairly challenging in sections. I think the AWRCS series typically has one of the more challenging course layouts of the various series in the area.
Other series in the area are CRA, NECXC, and the vintage one i mentioned.
Any type of off road race is only as much of a race as you make, a lot of guys enter these races and treat it like a trail ride, some are out for a little thrill of racing but not chasing trophies and others are out their to win. It's all good fun.
Those dual sport rides sound quite fun and laid back, for some reason i envision dual sport riders to be very welcoming and supportive. Probably a great riding experience.
That Hangover hare scramble is a typical hare scramble, if it was closer i would be interested, i'm spoiled for riding and don't like traveling too far, extra time spent driving could be time spent on the trail
Check out Mountain Ridge ATV park sometime, they have some great technical trails, lots of rocks, some really great single track as well with a few really tough sections. It's about 1.5hrs East of Pittsburgh give or take. They are closed now though.
Just keep on riding and pushing yourself, everything will fall into place especially for technical riding. Just takes some time and practice like most things. Advice i give people for technical riding is pretty simple, try and keep your feet on the pegs as much as you possibly can, try not to put your feet down unless you are going to fall for sure. That is a super good training exercise. And something that goes along with that, keep your momentum and just go over ****, don't worry about the perfect line through the rocks, if you get bounced off that line and there is a big obstacle in your way, maintain your momentum and just go over it, you'd be surprised what your bike will just go over.