I’d focus on talking about the features and location.

I've heard Stessa and Buildium for the most part but find it's actually very difficult to use for the average small scale landlord (I have 7 doors)The cost of Buildium I think is way too high for the small scale self managed landlord like myself. 7 units comes to $55/monthAs for Stella, the UI isnt the greatest and probably tailored for more property management companies, and the accounting features are rather lacking for Canadian tax laws.

And also you and others identified benefits I am not realized before now.I'd say to first and foremost make that clear distinction that it's NOT an "investment" that it's you, or anyone, starting a Business. 

I signed up for Deal Machine but it looks like they already removed the texting feature but I do like the driving for dollars function.

Looking forward to reading some of the responses.While you wait for recommendations, I suggest using the search icon to look up "rentredi" and "hemlane", another platform for PM that has a feature for maintenance coordination.The search results will show past forum posts where members chime in on the subject.

@Loretta Chang - Oh, and the reason why I am wanting to start this in Colorado and not Texas is first and foremost my wife.

The key features are the most important (square footage, age, condition whether it has a basement/garage, etc.)

First and foremost, congratulations on your graduation and pending job! 

They even have a feature to see any subscriptions you're being charged so you can make sure to "catch" any that you may have forgotten about.

Make sure where you sign up has this feature.