You said: "I think part of the problem was that my initial expectations were that these trugs were REALLY going to make me feel relaxed and care free. The don't really seem to do that for me at these doses, just barely. Are my expectation to high or am I taking a bit lower average doses that most people (at least what most people are willing to admit too.)"
I think you've hit it, your expectations are too high.
I've been trying to do a similar thing as you, experimenting with benzo's, but trying to stay away from tolerance. When i first took benzo's i did feel relaxed & care free, 10 mg of valium before a medical proceedure had me in an enjoyable state and 1 mg of lorazpam every few hrs. made the 2 day flight to India last winter tolerable, but mostly forgettable, I watched the matrix 3rd movie on the flight & don't remember it at all! i probably was eating the .5 lorazpams like candy, don't remember. I then went on to taking 1 mg, perhaps more a day for 3 weeks. Came home stopped the lorazpam & discovered withdrawal! I tapered off in week or two.
Next time I fly, i'll try valium.
You'd think i'd know better, but I've been using them again.
Now it's different, I hate to say this, but now all i notice is when I don't have any/enough benzo in my system. In other words, if i take some i feel nothing/normal, if i don't i feel bad; anxious, depressed. I was not able to keep my intake to once a week or so, it is every day.
Xanax, i can still feel; relaxed then sleepy, then depressed and feeling like having another pill. From what I've read on this board I've decided that xanax is too dangerous (addictive) for me.
I'm currently tapering off with klonopin (i don't feel anything either, but now I'm down to .5 K a day and plan to be done within a week.
The tolerance/dependency happened so fast this time!

I wish we had some pharmacists or MD's on the board who really could explain this stuff.
i wish there was an antianxiety drug that worked (for me)without dependence & other bad side effects.
Good luck with your exploration, keep us informed, this is one of my favorite threads.