Aaron,
I had signed up for a three day Tactical Combat Casualty Care class from Redback One earlier in the year, but it was cancelled due to not enough students. Jason Falla who runs Redback One is former Australian SAS and was a senior instructor at Blackwater after that. I think in SAS he was certified as a medic, maybe like the 18D in US SF.
At King 33 I had taken a CPR and a one day Buddy and Self Aid class, so I had dipped my toe into the subject. Jason took a couple hours each day around lunch and reviewed the material from the TCCC class. Basically we go some lecture, but no hands on. It was still very good.
Lately I have become a huge believer in the idea of packing away skills before packing away supplies.
Even a rudimentary level of medical ability will be a good skill to have, so I am trying to learn as much as I can.
The same goes for building up some stamina. Like you said, being able to hike with a ruck sack is a primary skill. I use my GR1 as my general gear back to go to my weekly King 33 training and for when I go to weekend classes. It is not packed as a "get home" or "get away" bag. I keep a smaller cheaper pack in the car for that purpose. What I am starting to do is to put these two 5lb bean bag weights into my GR1 bringing the total weight up to 19 lbs. I try to carry the 19 lb ruck as much as I can when out walking. It is taking some getting used to, but I can do about a mile now (compared to my usual two mile walk without it).
I also took a really good course from a guy named Mike Pannone. He was previously in Delta and later trained the Air Marshalls after 9/11. The class was called something like Covert Carry Pistol and basically covered how to carry concealed and to draw from concealment (plus a lot more). Over the weekend we did close to 500 draws from under cover garments. It was 40 degrees, heavy rain and 20 mph wind for the first day, so we got a lot of experience.
I also trained in the winter with King 33 where we practiced drawing while wearing parkas and gloves in 20 degree weather and 8 inches of snow. You would be surprised what you find out about your techniques and your gear doing this sort of thing. Better to find out now than later the hard way.
Of the traveling trainers, I have found that Northern Red (now called Invictus Group), Redback One and Mike Pannone were all very good. The first two market themselves and can be found via Google or Facebook. Mike Pannone markets via Alias Training, who also markets several other good trainers.
What I am finding from carrying the 20 lb ruck and from reading some other blog posts on the subject, is that you had better thin down your ruck contents to the bare minimum if you expect to carry it for any distance, especially if you are weak like me.
My new priority is: 1) heat making materials and minimal shelter (poncho and liner); 2) water and purifying equipment; 3) basic first aid kit; 4) minimal food like life raft biscuits; 5) some protective equipment; 6) second set of clothes or at least socks and mole skin. I have not actually packed this, but I am guessing that I will be close to 20 lbs with just the minimal amount of this.
I figure if you are looking to carry it for two or three days, you can cut way back on carrying food.