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REVBENT you have a pretty interesting resume! i have done a fair bit of drafting (in the trades my entire life), and i find that drafting anything with paper/rulers is far more accurate in the long than the software counterparts, however sincerely slower. it was very rare to find architects who's prints (software) didn't put point loads in between joists (non load bearing points). sure it "works" but to me that was always the difference from building a house vs a home.
Hehe, just to clarify, when I say architecture, I mean software/systems/web, etc, and not buildings...
I would say using one, it's a matter of context and what works for you. Transitioning from pen and paper to digital with a tablet does take some getting used to. Then, as for the software, the more you use it, the faster you get that muscle memory in with the features, hotkeys, etc.