I was hired by one of the owners of the Atomic Wrangler in Freeside to hunt down several people, including an annoying fellow named Santiago, who owed them money. I did this successfully, and was given a new objective: to kill someone on the strip. So far, so good.

Then, I spoke to the other owner of the Atomic Wrangler, and he asked me to recruit some "escorts" to work at the Wrangler. I managed to recruit Santiago, but upon completing that quest objective, I was given a quest update for the debt-collecting quest telling me to return 388 caps to the Wrangler. If I do that, then I'm given 300 caps in return (for a net total of -88 caps) and I'm asked again to kill the guy on the strip, but my only option is to decline the quest.

Does anyone know how I can complete both quests without problems, and without losing those 88 caps?