Hello! Yes, there are seedier establishments where he could work. They can be found in Olympia and Wyver, with the main difference being that Wyver's seedier establishments probably have some kind of connection to Cree, though perhaps not directly - he does not own a chain of bars, for example, but his people would frequent these places more and might extend an offer of protection to one or two, etc. In both cities they pay well enough to live slightly less-than-comfortably, and pretty much entirely under the table.