I’m older as well, my children are adults now so I’m super flexible and willing to move yearly for the next 5 years; at least in neighborhoods and multi family units  I feel comfortable living in. 

Currently my area doesn't have a lot of small-multi units on market in an area I'd feel comfortable living as a young female.

The underwriter will have a very high comfort level of the risk due to the comprehensive building review in their file.What if something happens to your building?

Going forward I would like to ditch the office and make my life easier by working from home but I am fearful of taking away the space that my tenants feel comfortable leaving rent or paying in person.

Get comfortable with your number and get ready to write offers.

If you don't feel comfortable amending a line or two in a Word document for your lease to address a possible change due to covid, then I would shop attorneys for price. 

Currently I live in an apartment and have a comfortable (but boring) 9 to 5 job and have around 90k just sitting in savings accounts. 

-Have a comfortable cushion of cash reserves, whatever that means to you.

I see from your profile that you are married so your wife would need to be on board with a year or two of less comfort via househacking in order to help build long term wealth.

They should be able to tell you how much of the potential rental income with count towards the income requirement and your CPA can guide you on how much you can comfortably afford in a housing payment.