This book has great information on how to evaluate deals and will tell you about the metrics you are asking.

However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.

I know I can get an insurance plan, but is it worth the headache?

Learn how to calculate repairs fairly accurately.

with that said, I don't know that seller finance will let you grow more quickly. 

How did you finance this deal?

How much will you spend in repairs on a 1920's house with renters ? 

To be honest the monthly payment doesn't sound outrageous given the possible items covered, but who know without the accounting...and any buyer should want to see that accounting when you sell, so sort the issues out now. 

As you guide landlords through that stressful process, you can introduce how your tenant screening and management services help prevent future issues.2.Focus on Rental Listings as a Lead Source•A highly effective way to grow your PM business is to actively market rental vacancies for landlords.

How would you suggest going about finding a deal and managing it out of state.