Despite signing on the court day that she would move out in 7 days and waiving her right to appeal, she still appealed, preventing me from filing a writ of possession.

You're right, I definitely do not want to force a bad deal just to avoid a relatively small amount in taxes.This morning, I spoke with the property assessor’s office in the county where my property is located.

A handy search bar in the upper right makes it easy to find previous discussions, blogs, podcasts, and other resources.

if you find the right deal in the right area with the right tenant? 

If you plan to scale, I would get one right away on your first property.

Once the time is right, with enough research, I would jump into a market (hopefully local if affordable) and get started.

Of course, there's no perfect right or wrong answer, it will be different for all but make sure you do what is comfortable for you and what fits your goals. 

It’s also worth connecting with a property manager and contractor early, even if you don’t need them right away.

If you can purchase this home with private money or seller financing and get a $110k loan, then you could do a rate/term refi right after so do a 90 or 120 day note to secure the property and get it in your name, then refi into long term debt using the full appraised value. 

I attend one in Frederick which is online right now.