I'm open to this but would like to charge a monthly pet fee or a one time fee (per a year long lease). 

TBD Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The borrower has been paying on time and the CFD purchase price to property value is <50% at this point.

I had at one time had the tenants billed directly including the water bills.

But- since you are a newbie, in lay person's terms, the answer is yes...but slowly and over a very long time. 27.5 years, to be exact. 

Lessons learned: 1) Do a more thorough tour of house before purchasing 2) Have more money saved Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

When I list a property I spend a lot of time ensuring that it's as attractive as possible in the eyes of investors.

A little about me, I'm 34, a full time first responder (with no intentions of leaving the job early) and I currently own 2 SFH's in Ohio and WV.

Also factor in your capital, time, energy, skills, and other resources.

Our first lead was very interested and eager to book but our dates did not align with pre-booked guests form Airbnb at that time as there was a bit of overlap from ending our STR and transitioning to MTR.