The answer to this is simple:
How do you want to play your game?
Possible answers:
-Characters are professionals, they call their price according to preestablished costs depending on the job they are called for. Just explain that this cost is more related to lifestyle costs, than shiny new toy, cyberware costs.
I use this way, and show the players a runner's document... that is... somewhere... on costs for jobs. As an example, wetowrk would be

5000, plus expected opposition, let's go very strong -magical support and some three or four bodyguards with lethal weapons. Yes pistols and live ammo count for these-, another :nuyen:5000, plus it has to be done within the hour, another :nuyen:10000, and no one should know who did it/why he did it, another

5000.
Medical and ammo expenses are covered by the Johnson, either in previously delivered equipment -hands out a few clips or regular ammo and medkits, for example-. These are seen as good faith prepayment offers.
Also if the run needs particular things, the Johnson should provide them (Need a boat, he pays for it, etc). These big costs should be delivered back at the Johnson. If lost during the run or too hot to be given back, he takes the hit for it.These may be negotiated as par tof the payment ("Nice, I got out that new Wasp personnal helicopter out of that run!").
I try to make that said prices charged are enough to keep the lifestyles. Their job costs (program degradation and such) are not taken as aprt of lifestyle costs. Except for high and luxury, but that is more a house rule and handwavium on my part than is necessary for this discussion.
This makes the gritty atmosphere I like going nicely and makes the runners thik of other activities for their characters. This tends to help character development.
-John Woo style, hand out loads of money. This will ensure characters can buy deltaware cyber and go nuts on crazy shopping sprees. Milgrade armour with enhancements is easily restored. High connections contacts are usual. Johnson can hook the players with military grade providers if they pull off a good job.
-Gang Style, they sweat for a damned used Ingram Smartgun. An Ares Alpha? Makes you the new boss on the mean, dark streets. Improvised weapons and chains are favoured in many cases, shotguns are some of the most powerful guns you can get your tattoed hands on.
Stealing vehicles is a way to increase the profits.
Prices were given only on the first possibility, and then only as an example, YMMV. Tailor it to your campaign and the player's wishes. I favour creativity for getting gear or toys instead of simply paying it via Master Card, others want simply to shoot things and get straight combat excitement.
Listen to your players, they are wise; but never sacrifice your fun just to deliver.