The way I like to handle Lifestyles is to make a judgment call when expenses come up. Anything that is out of the ordinary for the character's lifestyle is something you need to pay for. If you have a High lifestyle you never need to pay for dining, prostitutes, sporting events with modest seating, etc. But if you want to fly to the Bahamas, that is going to cost you. If you want to sit in the front row to watch the highly anticipated heavyweight boxing title fight, that is also going to cost you. But let's say you only have a Low lifestyle, now things like prostitutes and fine dining are not free. You can have some potato chips and perhaps some cheap booze, but the moment you reach for that fine bottle of whiskey I'm going to let you know that it's not included in your lifestyle. It gets worse at the Street level, you now have to pay for everything, even things like a bottle of water or a cheap cigar.
Handling things this way makes players feel like they're getting their money's worth for forking over 10k+ per month for a High lifestyle. It also makes someone with a Street lifestyle feel the pain of being homeless. And at that level I'm going to make it tough for you to get by in general, you're going to be struggling for food, warmth, safety and even to get relatively clean to present yourself ot Mr. Johnson. People are going to treat you poorly, but your buddy with the High lifestyle is going to be treated rather well in most civilized places.