Most of the problems here sound like they are about support from the development environment, not the system itself.
(well, objects floating away means you need \FloatBarrier -- and most times I used wrapfig, the caption evolved and at the end I realized a float fit better)
I found that I cannot hack with LaTeX without internet, and that’s pretty worrying. But it’s because I have no neat local documentation. Too much expert knowledge, too little clear and structured documentation (except for the documentation which is restricted to single packages). That does not sound like something which needs a rewrite.
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