The best time to invest is always in the past, but that isn't possible, so the only thing you can do is start today.

It’s a smart move, especially since it ties in with your goal of saving for your first investment.For skills, you probably already have a good foundation with your sales experience—things like communication, organization, and dealing with clients are all super valuable.

Seconding what @Max Wilhite said, Multi-Family is a great way to get started.

I am excited to get started on the next one. 

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.

In my personal experiences a lot of structural items start with bad drainage.

I've worked with some Canadians buying  here in Ohio.Indeed, rather than selling your stocks to fund investments (and lose out on any potential price appreciation and dividend payments, as well as incurring capital gains taxes), a nice alternative is to borrow against some percentage of the holdings.You would start with the brokerage where you hold the stocks and see what their loan program looks like for the account you hold. 

It will be a while before the negative equity starts to be recovered.  

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

The numbers are in line with anyone who starts a business, it's like a 90% fail rate to be an entrepreneur.