in 3 years, I can only think of 3 times we actually had to do this so you make a good point as to whether it's actually worth executing on it in fear of a poor reviews. 

It would seem to me that a landlord would be too afraid of raising rents for fear of losing tenants and upsetting the DSCR going into year 5.

My fear is I put my foot down and she gets insulted and does not feel the want to re up her lease in March.

My guess is you are holding yourself back, fear of failure or similar.Once you find what you think is a good deal, run it by BP if you like, but don't be afraid to commit!

I know there will likely be some challenges with the first one, but I'm hoping that once I get it under my belt I'll realize that most of my fears weren't even realistic fears at all to begin with.

My biggest fear is what if you get an offer accepted at a relatively high percentage on the dollar and cannot find a buyer?

I do not want FEAR to take control of my future. but i don't want to be stuck paying another mortgage that we cant afford right now. any advice?

If you have any advice on appeasing that fear it would be appreciated.

Fear is a funny thing. 

Fear overtook me for a short while and my confidence was fading quickly.