My knowledge and subsequent track record has been one of basically following the wagon of friends and family(which as you can imagine has turned out to be a disaster). 

I think you're on the right track in terms of it's proximity to other MSA's.  

One of the biggest challenges for everyone involved is being on the same page about the actual time required for maintenance.DIY landlords rarely properly track their time when it comes to property management in general - tracking their true time invested in maintenance is where they perform the worst.Investors that hire PMCs are rarely any better at understanding the true amount of time maintenance takes.

I own a mortgage company, so I have my loan officers use this Fannie Mae income calculation tool for all business for self borrowers: https://singlefamily.fanniemae.com/applications-technology/income-calculator .

@Natalie Kolodij is on the right track with her questions.

Without a closet is would be referred to as a office or study.

The time has come for me to start investing in real estate and before doing so i'm looking to build a strong and dedicated team of partners: agents, lenders, contractors and property managers mainly in the Cleveland area (but also open to markets within a 2-3 hr drive away) that already possess an excellent track record in their line of work and that value long term collaboration.

I track the principal as a Liability account in Xero, and whenever I add it to a report, it always shows the current balance, rather than the change over the chosen time period (like with expense accounts).  

I'm calling my local office tomorrow to find out.

People in my area live right next to train tracks and there are loud trains shaking the place at all hours.