If I were you, I would start this way, if you are new to real estate investing.

Why not start thinking bigger?

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

Guests cover the cleaning cost.

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.

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

I was hoping to do a deal and get my feet wet with something relatively simple to start.

Thirty years ago I started purchasing and living in properties in upcoming inner city neighborhoods that required renovation.

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

Get them out and start with leases and only rent to people that you have screened.