My advice would be to start small and do your research.

I don’t have a specific recommendation off the top of my head, but for HOA/condo insurance, it’s usually best to start with a broker who specializes in multifamily or association policies.

It really helped us a bunch as we got started a year ago.

If you used them to purchase another rental/ use for another business endeavor...the process starts over. 

You may want to start with the BP agent finder for those markets and then work with them to find good PMs and lenders.

I'd start talking to her and looking for another place for her to live. 

Then sell the property and start doing fix and flip or fix and rent. ( I prefer to sell this property as it 100km away from my student rentals. ) Not sure if I should renovate the lower unit to sell.

I myself don't have a lot of appetite for risk which is why I started investing in real estate.

Then, in April last year, my husband and I started a business, and I temporarily put both of those on hold while taking care of my dad.

We quit real estate investing and it took me 23 years to start again.