If the plan to do this remodel is based on the idea that contractors are hungry for business, I would talk to a few first. I am not so sure they are hungry for business at all.
If the economy goes into recession due to the virus it could take months for the construction industry to feel it. The housing market is not like the stock market. It turns pretty slowly.
With that said, once your permit is ready to pull you can wait quite some time before it expires. Then, you have 6 months after pulling a permit to call for your first inspection. My thought is – start on the permit now so you can pull it once the market softens.
I like this plan because being in a rush makes dealing with the city more difficult. It seems smoother when you aren’t in a rush because you have time to do any stupid shit they make you do so the requests don’t seem so frustrating.
Getting a permit like the one you need shouldn’t be too bad. I would avoid an architect – just draw up a floor plan on your own and find a structural engineer on yelp to do the construction drawings. If you are not much into DIY, consider a design-build contractor that will do floorplan, structural, pull the permit, and built it for you. I do my own general contracting and don’t mind dealing with the city so I don’t like this option and they may not like you playing games with the schedule as I mentioned above, but for a rental owned by a non-DYI person it can be a good option.
The permitting process is actually quite organized down at the city dept of development services. Just make an appointment to pull a construction permit and let them walk you through it. The first step will be to pull zoning maps with all the overlays you hope don’t exist. Play dumb, be super nice, ask lots of questions like “what is next” and “can you make a list of all the things I need” or “who can help me with that?
So, that is my thought – start on the permit now. Take your time, maybe try to do it on your own, or with the help of a permit runner. Once the permit is ready, if the market hasn’t softened just wait to pull it as long as you can. Then pull the permit. If contractors still busy, wait to start construction up to 180 days and call for your first inspection, which might be a pre-construction meeting anyway.