Pablo Riviera is the owner of a swanky, big shack that serves great spirits and good fun... well, it used to before the Brotherhood of Steel war. Unfortunately for Pablo, those happy days are gone. His regular supplier of alcohol, the 3-Some Caravan Company, has not been able to get fresh stock to him for some time. No hooch means no customers, and poor Pablo is feeling the pinch. Since he is a proud man, he refuses to give into pressure and strong-arming from the Crimson Caravan Company, so he sticks with 3-Some, who always gave him a fair price and respect. Thus, Pablo the barkeep is about as destitute as can be. He'd drink himself into a drunken stupor if he had enough liquor, but he does not.
Get liquor for Pablo: Dusty's Desires, who do business with Crimson Caravan, are well stocked with alcohol. The Crimson Caravan refuse to sell to Pablo until he severs his ties with 3-Some, which he won't. The Prisoner can bring what alcohol they find and sell it at a good price to him or escort some of the 3-Some caravans, however these are only short term solutions, ending the war with the Brotherhood of Steel would be the optimal path to restoring the balance of competition. In addition the Prisoner could expose Crimson Caravan's illicit activities and have them closed down allowing 3-Some to take advantage of the void in the market.
Pablo has a two bedroom shack overlooking the toxic lake for sale, the Prisoner can buy it for a highly inflated price, although helping Pablo with his liquor problem will see him lower the asking price dramatically.