Make sure you have a lot of ducks and all fo them in a row. 5 year estimates on revenue and expenses, full business plan, licenses etc etc all in place before you go in.

I have had permits in other jurisdictions be quite easy.My view is I would let someone familiar with the process do it unless you were planning on applying for many permits over time.  

I look forward to hearing from the nominee on his plans to help spur more economic progress in more under-served areas like the ones that I live in, work in, and invest in and hope he will help extend and expand the Opportunity Zone Tax Credits. https://www.jtcgroup.com/insights/opportunity-zones-have-done-what-they-were-created-to-do-will-that-be-enough/https://eig.org/opportunity-zones-research-brief/

What do you plan to do with your license?

House hack if you can, pool funds for a local investment if you can't (get an agreed exit plan in place first).Remember, you may not even like being a landlord.

I plan to purchase another Multi-family in the next year or so (sooner if the right one comes along).

You haven't provided us with any information that would help us help you.My recommendation: do not sell a property unless you have a plan to invest it in another property that will perform better, or if selling will move you closer to your goals.If you don't have a firm plan, hold onto it until you do.

@Stuart Udis plan A was to reposition as small office and keep it that way.  

I would need to know more specs on the house but with material shortages It's difficult to say how much to budget. 80K-120K for full gut perhaps but unsure with lumber beings so expensive and shortages.I would plan 9 months of vacancy between the pain you will endure pulling permits & having your contractors show up everyday to complete the work & then final inspections to get a CO. 

Quote from @John Williams: I recently bought a home that has an attached dwelling unit where Im planning to move in and rent out the main unit.