Glimper,
As stated in my above post, there are TWO ways to obtain a skin. The 1st is during an Admin Skin Event such as the one that took place about 3 or 4 weeks ago and that was completely free. The 2nd can be obtained when donating, however, you can ask for MORE than just a free skin. I for example asked for a skin and the unique car. As for donating itself, a person can easily lose 5 dollars just sitting in their couch, I don't see the big stress on saying "OMG it's REAL money" but as I said you're more than welcome to wait for a free skin event if money is that tight.
As far as belonging to other factions, as stated on the site, you're permitted to belong to other factions with your alt so long as you keep both separate and don't use info or resources gained in LHM for the benefit of an outside character or faction.
I understand your concern regarding "late in the session" however, what's stopping people from having fun now. We've all been waiting on a wipe that is taking a lot longer than expected. If everything was to late in the session to play, then there would be no point in playing at all.
I thank you for the luck and I wish you a great gaming experience.