Well, that was a wrench in a hastily conceived plan.  She had better developed instincts than he thought.  Tailpin would have to level with her without actually leveling with her.  Awkward... awkward and difficult.  He looked at her for a long moment, leaving the trade window up.  He did notice the more timid girl leave but had little chance to address her.  Besides, he wasn't sure how involved she was going to be in the future of the group so he had bigger current priorities.

"As for that wager, it was an attempt to hurry everyone into town before the monster's behavior algorithms changed after sunset.  And..." He paused briefly and looked like he was momentarily at a loss for words.  "Paying for the inn is... a guy thing.  The rest is because time has always been money and we don't know each other well enough for me to expect you to do it for free."

"As for what I get out of it personally, I'm a thirty year old trapped in a death game that centers on swords.  I am level two with absolutely no aptitude for swords.  A level one monster nearly killed me on my first day and I failed to scratch it until I switched to a bow."  He drew his starter shortsword and held it out.  "This might as well be virtual rubber.  I have no ability to defend myself in close combat.  I cannot fight a boss.  I cannot do anything directly to free any of these people who don't want to be here or change the balance of power.  My strongest skills involve long distance mapping, shooting, and spotting which are of greatest use in field zones like those around towns."  His voice was flat and businesslike.  "I need to be able to make a living at least.  How would helping out a budding entrepreneur with seed money and possibly getting into her business on the ground floor as a supplier, when my skills can still earn a pretty penny quickly and have plenty of room to develop, not be in my favor?"

It was just at that moment that another person approached.  It was the guy who arrived with good intentions too late to do anything.  Still, he might be low enough level to profit from the plan as well.  And, he was socially awkward.  Still, possibly charming in the right company and undoubtedly better than Tailpin with a sword.

So, now he had two possible nocturnal companions to keep his eyes on while having to haggle a budding merchant into accepting money to deliver money where she was probably going to go anyway.  His head was starting to hurt.  There was no guarantee that that beta-tester with the debonair mask was going to hang around long enough for a lengthy explanation.  He had to make this brief.

"Sapphira, to make this brief.  I have two people in mind for a brief nocturnal excursion and one of them isn't truly aware of my presence yet.  I intend to help you and profit in turn, if you agree.  I will need to rapidly improve my abilities if I am to help you keep up with demand."  Then he turned to the new arrival.  "You, hi.  My name is Tailpin and this is Sapphira.  I could actually use a blade to help me out for the next couple hours while I map the surrounding area after dark and test the nocturnal algorithms for the local monsters.  See that guy over there with the scythe?  I'm planning on trying to recruit him too since night fighting isn't going to be so easy for a level two archer in a level three possibly level four field, depending on what's outside the other town gates, and more blades are typically better."

So now he was waiting on two decisions and only had to keep one person in the corner of his eye.  Sapphira wanted his intentions and he'd just spelled them out.  The new guy wanted to chat but this was the time to take initiative.  They could talk on the way.  Then again, there was the possibility that Sapphira would want to come along too.  Unlikely but possible.  His contribution to the earlier fight had been limited and at long range.  She might actually want to observe up close now that he had stated his interest in joining her business.  Untimately, he just really didn't want to miss out on the chance to work with another beta-tester.  He might even be able to convince him to join up long-term, not that he was getting his hopes up or anything.  That guy could probably fly solo for awhile yet.