Any advice you would give to someone first starting out?

To answer the first big question in your post — single family vs multi-family — I am firmly in the multi-family camp.

Hey Everyone,I am an extremely novice real estate investor looking for some advice on an opportunity I have on the table. I have the option to buy a 1,300-sqft 3-bed, 1.5-bath house in South End neighborhood of Stamfo...

Horror story #2: while selling off one of the Class C Indianapolis properties, buyer asked me to pay replace the sewer line before closing... absolutely not...here's a partial credit (check to written out to contractor from closing proceeds so buyers don't pocket the money) 

It’s a blessing (the reason you found real estate in the first place) and a curse (you probably get distracted easily on what asset class to focus on).

I am new to real estate investing, and is considering house hacking a property for my first deal.

@Amanda Bradley Tenant sounds like typical Class C with a credit score under 620.How hard was it to find this tenant?

This was our first home, and learned it all along the way.

Skip the class and go straight to learning on the job.

In fact, I would estimate that it is mostly upper middle-class folks that have the money and wherewithal to go through the vacation rental process - prepayment of substantial monies, etc.If you only have one property, I would just stick with Venmo, CashApp, or Paypal.