She has been not the greatest employee and they want to let her go but were afraid of a lawsuit . 

I would be afraid no one would want it unless i already had a buyer!

Agree - if you are not afraid of reno then the approach might be different. 

Pick up one mid to LT rental in a high medical community outside of my current market.I have always been afraid to leave my current market and I want 2025 to be the year I get over the fear.Be more involved in economic development in my current market. 

I am afraid we will fall for a property with a false sense of a good deal.Are there any suggestions to help me run an analysis that would better account for the larger down payment and allow me to better analyze potential properties in the future.

I want you to feel the pride in being told all your accomplishments over 10 or 20 years are pure luck by someone afraid to get started.

The radio example you shared really drives home the point: what works in one market might flop in another, but the key is not being afraid to pivot and learn from it.I also really liked your point about keeping the reps up.

I’m afraid she’s going to turn into a squatter 

In other words, if you don't fill your unit in the slow season because you're afraid it will cut into your high season revenue, will the high season revenue more than cover the difference?

Don’t be afraid to use your knowledge and jump in and do that first deal.