It sounds like you are just having trouble pulling the trigger. 

Hi Amanda,If they are trouble tenant then you should probably provide them whatever the notice period is in the current lease and just have them move out. 

I have some flexibility but rely heavily on my team for admin work and the day-to-day operations of property management.

Sometimes I have even directed troubled tenants towards assistance programs (such as single moms because there are a lot of programs for them specifically in my area especially).

Tenant stopped paying rent before 2 months of the lease expiring, property manager filed for eviction process but tenant vacated the property before sheriff served the notice.

Those 7 years were cash positive, but we just weren't making enough cash flow to make it worth the trouble. 

I am planning to get into the TN real estate market as my first investment and am looking for some information.In particular: Areas to steer clear of, property management fees, typical cosmetic rehab costs, etc.My strategy is to put large down payments on 2 properties (relative to housing prices) to help pay for my living in NY while still gaining appreciation in a growing real estate market.

I'm barely competent managing rentals in my backyard in NC. 

Yes, I am looking for an online platform to begin self-managing too.

@Gary Abrams A cloud based solution would work really well in your scenario of having other family logging in and helping with management.