Imagine making millions of dollars over the course of your career and then having to pay 30-50% every year to uncle sam instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they just buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of best ways to end up with a much larger net worth at the end of your career.

If the only MFH options you're finding are in areas you're not comfortable with, it might be worth focusing on a duplex in a better neighborhood.Saving up for a larger property later is a valid approach too, but keep in mind that real estate tends to appreciate over time, and waiting might make it harder to enter the market later.

There are likely larger users out than than what I deal with, but at that SF at least in my world you are likely looking at multiple tenants, not sure if thats what you planned or not.additionally something else to consider is the cost of buildout on a med office space. depending if they are going to have x ray or not its not uncommon to see $500-$800K buildouts in my experience. 

What sorts of questions can I ask her to learn how much risk this is? 

I'm not an attorney though - you know the drill.Regardless, consider contacting your insurance company and letting them sort it out with the neighbor's insurance company.

And many DSCR lenders are no Registered Mortgage Loan Officers (RMLOs).You will need to get a conventional mortgage for your refinance of some sort if you plan to live in it.

I guess they can feel blessed they weren’t crushed and sent out of business by the rampant theft that forced closures of even larger and well funded grocery stores in Detroit, Chicago, LA and NYC. 

All the best You said it correctly, one without your experience in an area would need that app.The app pulls comps for hundreds of properties, and then it sorts them from highest to lowest margin in under 2 seconds.

A good condo board should be saving money for larger projects as they are known in advance (eg every 25 years you need a new roof). 

This https://thestrive.co/pace-morby-net-worth/ jumps into trying to sort out his actual income and net worth but even then, it's a big question mark.