We're breaking down the financials together so I can ensure he is confident in moving forward and understands the risks involved and how we will mitigate the risks along the way. 

You risk far more health danger by having it torn up than by just leaving it alone and covering it with something that doesn't require grinding, drilling or punching holes into it - like a floating vinyl plank floor, or glue-down CVTs, etc.

Even developers/flippers can enter deals to mitigate a timing risk.

You are putting them in danger, you in danger, and the rest of your building in danger.3.

To answer your question, STR is the better money play to mitigate some of the risk HOA costs present.

In any case, I do think there is a need, and I do think that I can mitigate some of the realtor concerns about professional tenants vs. multi-family 2nd floor and above.

I know enough about a lot of things to be dangerous, but lack detailed expertise and certifications.I will say that I was extremely disappointed with my last realtors lack of construction knowledge so you will have a leg up there for sure, and you should play up that as a selling point

For someone who is new to real estate, what will be the best way to find out about auctions. and how do you mitigate the risks?

I think house hacking and investing in your own back yard is the best way to build confidence and mitigate your risks.

Well...For example, red means danger, warning, run, wrong, watch out, YOU WILL CROAK!!