You seem to have found most of the answers yourself, but I'll try to pitch in a little info.
Game difficulty is based on the CGL(Current Game Level) which is raised by doing main quests(Govt or rebel). In some cases you can advance the CGL's by killing enemies, but for the most part the levels a locked at certain missions.
DO NOT EVER order a car from Rico, it will never arrive and you'll lose the mony you gave him. He will sell you the Willies jeep and the BTR, but you need to have the money to get that option in the dialog.
If you play with the BFX mod you can buy all available cars from Billy.Bob at the Sectret Harbor. As with Rico, you need to have the money to get the dialog option to buy them. Here's a price list:
GAZ69 for 50000
Willis Jeep for 60000
Hummer for 200000
Ural truck for 300000
BTR-70 for 1000000
FMTV A1R for 2000000
As for the Bobling missions, look in your Journal for more clues and directions on how to solve them.
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