Some of the statements you put in your original post make me think you have some kind of emotional connection with this tenant which is a big no no..

As you can probably imagine, becoming emotionally attached to this home is super easy.

and the letter might be more for someone emotionally tied to their house, not a income property, but hey, no real harm in trying!

"I am leaning toward a $100/month reduction" You are leaning in the wrong direction by allowing emotions to drive your business.

Duplexes, etc sell for a multiple of rent....no emotions.

For many, it’s not necessarily a dollar barrier, but rather an emotional connection.

I won't go any lower and I am definitely going to keep emotions out of this.I hope to hear your feedback!

Keep Your Emotions in CheckI feel like many of these have been analyzed at length within some of the Bigger Pockets podcasts but that everyone should really dive into what each one of them means for them. 

@Andy Mirza I went over the report with the appraiser, the only Comp I questioned was an REO in the same building that sold two  months ago that was badly damaged, water damage in two locations, old carpet, damaged kitchen floors, broken HVAC, nothing new or upgraded and that unit sold for $234,000 as an REO.Is my agent a good one is definitely a good question, After the latest price drop I told her this isn't my primary residence so I don't have the typical emotional attachments some sellers have where they want the highest prices in the neighborhood, Do we have to do these incremental small price drops, I just want what the appraisal/market says it's worth or really close to it so lets get it sold, that's when the discussion about not pricing it at appraisal came in due to the buyers wanting concessions/discounts.I didn't know over 60 days on the MLS was happening in some markets. 

Family will play on emotions when trouble hits.