That is a choice you'll have to make based on risk and your wealth building portfolio.

Or does it purely my choice of whether I want cash flow or equity build? 

If you just have a couple of rentals, a cheaper and simpler module like Buildium would be a good choice.

Yup Xero is a good choice.

A choice to live OUT LOUD, or tip-toe to an end. 

If the market cycle changes; if your area of interest isn’t right; if you don’t have sufficient capital or credit; and if your not a “fit” for the work necessary to close the transaction, then you might have thrown $15,000 or $40,000 or MORE down the drain.  

Milwaukee is my firsst choice then Im looking at Cleveland Ohio.

Give them a specific amount of time to clean it up or face a penalty. 24 hours should be more than sufficient.

I currently own a home in Hawaii, unfortunately my family and I are moving and we want to make the correct choice.

One of the recommendations I've seen here on BP is to hire a virtual assistant (VA) to manage the property using the software of your choice.