I am not in MN so of course, our markets are different but in PA they are starting to go more digital with records.

No system is perfect, so don't waste your time chasing after the next shiny object.

I set us some objectives and looked at where I could get my target investment returns while taking a reasonable degree of risk.Hope this helps in your reflection.

It's a lot easier to hold onto a property and wait for the right time to sell if it's breaking even (or cash-flowing obviously), than to look objectively at market trends and find the right time to sell when you're paying into the property every month. 

I'd like to find a great digital lock box or smart key, something where I can give a prospective tenant a code and then change that code.

I've found the idea of objection handling to be highly overrated.

Be careful going below your standards, and always document your objective reasons for choosing one applicant over another. 

This bleeds over into the PM understanding the investor's goals and objectives for the property, and thus screening tenants, maintaining the property, minimizing expenses and vacancy, and maximizing rent collections accordingly. 

However, while I was succumbing to shiny object syndrome (admiring the fancy new kitchen, new hardware, and beautifully tiled bathrooms), my agent was crawling around in the basement crawlspaces, collecting cobwebs and assessing the plumbing.

In short, what I'm getting at since your strategy is buy-and-hold, is self-manage.In the beginning, I recommend you learn how to manage your own rentals especially when you have single-digit quantity rentals.