How you can get around these situations is to clearly state before you leave how much you expect people to pay. And you can do it in a good manner where nobody gets offended. Something as simple as "Wolfie make sure you have enough cash when we leave cause I cannot cover you once we do leave, figure maybe $100.00 bucks??". Something like that.
In all the years I have traveled with people ive traveled with cheap ones, not cheap ones, rich ones, poor ones, planners, non planners. Each type is a challenge and you need to work differently with each type.
Keep in mind there are only two true types of individuals in this world...Leaders and followers. the leaders call the shots and the followers have to honor it.. Its just the way it works
Couldnt have said it better myself....well done!! lol