We're wondering about various what-if's though, such as what if the people tear up the place, what if we don't want to rent to someone in particular due to references or credit or pets, etc.

Some counties in Indiana would refer to this as an Accessory Dwelling Unit. 

I'd recommend speaking to a referred lender to help you understand all of your options.

This post is intended to be a response to your list as well as a reference for myself in the future!!

Do you know what they are referring to with the 5 year return or earlier where they talk about returning your initial investment?

Would love some actual reference to data if you have it (not anecdotal). 

References?

I thought to myself and thought the workshops must be very intensive.For me, the 3-day Real Estate Workshop was held at Roosevelt's Hotel.First Day:I was given two booklets--1) Real Estate Workbook (wich supplements the book they gave out before the workshop)2) Real Estate Elite Workshop Events Catalog (which I first thought was the daily schedule for the workshop but later found out it's an information packet on the $39,500 "elite" courses that they sell)The ironic part is that, through this three-day event, the so-called instructor Jason Jones referred to the Ad packet "Real Estate Elite Workshop Events Catalog" SIX times (he literally asked us to take it out and flip to certain page) and didn't mention ANYTHING nor asking us to read the "Real Estate Workbook ".

I am definitely referring to a house that was already insured as a rental, not as a primary residence.

Can you put one on Houfy or similar site.You can always have one on YouTube and reference the link.