yeah its pretty easy to run out of money (as in going negative) for a while in the beginning...
also a gang costs alot in the first weeks (~100gold each day), yeah they "can" get you +400 gold with stealing jobs... but overall i think its better not to use a gang in the first months.
and try to get several girls simply with "walking around town" and add them to barmaid/waitress/cleaning/security/customer service/catacombs.
prioritized "barmaid/waitress", girls that are c+ in combat can go to the catacombs a bit or work at security (carefull security costs 70gold a day so just add a girl to it if it goes into negative and stop at +50 or so and send her back to catacombs or customer service)
cleaning and security doesnt requite a girl every day... just add one to it if it goes negative security to get into +50 or so again or when filth prevents alot customers, then add a girl a few days to get to 0 again then stop.
so after a few weeks you got a few girls from walking around the town (think by default its 80% chance to meet someone (think in my games i lowered it to 20% in the config... as it was too easy to get a girl all the time)
and slowly you make money with the barmaids/waitresses
and later add gangs and buy girls from the slavemarket.
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as idea for wm-ex:
maybe a "brothel-advert-setting" could be something... similar to how you allow/disallow specific sex acts in the brothel setup screen, above in that screen there could be all the jobs listed as selectable and when you select some
i.e. singer/entertainer/whore each time a girl goes to the advertiseing job she has a 25% for each picked option to extra advertise that job... that way you can get customers wanting these jobs that unlock later (i.e. whore) a fit earlyer through advertisement.
so i.e. people who like to have just a gambling hall and not a bar could add all gambling jobs to it and with constant advertisement you might want peopel just in gambling and noone wants a waitress.
or maybe just concentrate on the whore jobs and no bar ones.
if a girl advertises she as normal advertises the brothel. and each selected special job option has a 25% chance to be advertised too (or a % chance based on how good the girl is in advertiseing =
e= 5%
d=10%
c=15%
b=20%
a=25%
+/- 10% randomness factor
or something similar
and sucessfull advertisement might add 3 points into bar stripper and each day that passes without advertisement it lowers by 1 point, so after a while people dont want it anymore and it requires constant advertisement to make people interested in the jobs that they are not "normaly" interested in.