@Rob Buffington Being that it's less than 5 units, an appraiser is going to use the comparative method rather than the income approach so you need to get some good market comps.

I think my future real estate strategy will take a two prong approach.

I've had a rental house for several years now, but am interested in taking a more serious approach to real estate investing. 

If you simply want to choose other investment or passive income approaches, then P2P lending, dividend stocks/mutual funds, carefully selected growth stocks, etc can provide that.  

You don't need to do all the dirty work or work out every detail, but you need to trust your people, and they need to trust you, too.I think in your heart you know the right way to handle business, you just don't have the understanding of your approach with people you hire to handle your business.

My current situation is, my grandmother lives in a retirement community near-me and has had some passings in the last couple of months (this is where probate comes up) and I was considering approaching the new owner who just inherited a property from there deceased loved one.

Lots of ways to approach this kinda thing. 

I would never suggest this approach to others without first understanding their strategy and an understanding of risks involved.  

If I was looking for a pure tenant, and not a roommate, I would have definitely used a group showing approach, but because I wanted the chance to meet these people and find out if they were killers, I also needed to get to know them Finding a new roommate/tenant was an enjoyable experience.

It is also probably the more ethical approach.