This topic has been discussed in the city council a lot recently. Here's a summary from their October discussion.
"Just minutes before the clock struck midnight, City Council approved the last amendments to the short-term rental resolution. The amendments, though not yet codified, were fairly significant. Most significant was an amendment from Mayor Pro Tem Kathie Tovo that will “phase out” commercial Type 2 short-term rentals in residential areas. Tovo also proposed amendments to make short-term rentals ADA-compliant and impose a 3 percent cap on Type 3 rentals, which are located in multifamily buildings. Both of those amendments failed. Council Member Leslie Pool proposed the last amendment of the evening, which asks staff to lower fees on Type 1 STRs and raise fees on Type 2 STRs in a way that is revenue neutral (the exact fees have yet to be worked out). That amendment also passed. Now that the resolution is complete, the ordinance process will move through the boards and commissions and Council committee process before heading back to City Council, again."
In November they put a moratorium on Type 2 licenses. Here's a link to a report on the November meeting. Point being, we've got a crazy mayor in right now and this topic is in flux, so the answer to your question could change monthly.
That said, for Type 1 licenses, the path still seems clear...and lucrative.