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

Tough situation.Sounds like your mortgage forces your hand. 

So I start with the sponsor first.

Either way, you have options which is great to have at 22 years old with equity in hand!

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.

You can wargame scenarios to decide what you think is best.On the other hand, that is a pretty sizeable rehab budget. 

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

I just don't want to start working with a realtor and waste time and end up with no real solid prospects for buying.

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.

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