I wish I had a solution, but if I go out with friends with limited means, I let them chose the restaurant. It may not always be my choice, as I prefer and don't mind spending more for memorable experiences, but I'm good as long as the company is nice and genuine. It's also not always good to pick up the bill in those places as it makes the relationship very unequal, and I don't like that either. For travel, I usually travel with like minded friends who have similar budgets and tastes in hotels and restaurants... so we haven't had much issue there.