@Andrew Michaud I would focus your spend on what will generate the most income for you either through increase rents or reduced expenses.

The numbers tell me I will make ~600 per month including all the expenses on maintenance, vacancy, etc.

Again leveraging your PM skills and passion, you can partner with others to tackle multiple deals and be an active investor to support your living expenses today. 

It's a bit more expensive up front but saves a ton of money in the long run. 

Just wanted to see most expensive homes people have purchased that actually cash flow?

Being an agent does save you the commission expense so that is great- It does take work, but sounds like you are ready to get it done!  

I would increase your CapEx and Maintenance expenses (I use 10% each for older, lower valued properties), but I err on the conservative side. 

Not so much 1,000 cash flow (I also assume you are talking about actual net income after expenses, including ongoing repairs, management, replacements).

@Filipe Pereira Thank you so much, I will look into that.Also on a side note from your other posts about potential heavy expensed utilities such as HVAC units, water heaters, dishwashers, etc., although having cash on reserve for repairs is crucial,  I would suggest purchasing a home warranty for your properties, to have a little piece of mind. 

They also pay operating expenses and utilities, which is the other two of the triple net.