I went to Hub city, shoveled some cow poo, traded shovel for a knife, then cut fibers from the red corn, then went to the far "SE" corner of the city map and used workbench to make rope, sold it to shop for around $94-100 caps each. Then bought a gun and leather armor and those rats died like dogs! Or.. they died like.. rats?
Get the Sad Wife quest in OldTown Hub, move some boxes, get Wasteland Band quest from guy in Maltese Falcon, get the Son of Bob quest from Iguana guy, level Outdoorsman to 100+, go to Gunrunners and talk to guy for some weapon skill boost (look it up), go to Adytum and talk to combat armor guy for Scavengers location, talk to leather wearing woman for a quest (instructions are wrong), go to Scavengers to find missing husband (talk to guys by hanging corpse), go to Library in boneyard to get "A Man's Job" quest, then take train to NCR station, then go to NCR and talk to iguana guy, talk to Mitch (trader) for his quest, then talk to mutant in Rawhide bar and Mira (bartender) for her quest (when you deliver her debt talk to guy in corner for Cautious Nature perk), then back to NCR Train Station, talk to Ranger Captain to finish Son of Bob quest = Combat Armor MK2 and caps and a gun.
Stash armor in tent.
Go Necropolis Watershed for Elmer quest (read the tape, don't need to carry it).
Then finish up loose ends.
Maybe get Cautious Nature as soon as you have 100 OD.