of all the threads ive read, this is on the books for uniqueness 

This is a duplex with a carriage house, so it's somewhat unique in this particular neighborhood.

In my opinion you will need someone who is going to get in the trenches with you, role play conversations with you so you are ready to talk with sellers and handle their objections about your commission price, why their house isn’t a worth $20,000 More than the same model down street, and why they choose a new young agent like you and I vs a more experience agent that has sold 100s of homes in their career. 

Set your objectives first, then it will become clear if this is a good deal or not.

This is also a rule of thumb, and each investment is unique, but general speaking I try to stay away from markets that have a declining rent trend.Where to find information?

That said, i know Im 2-3 years out from achieving that objective should i execute the right strategy.  

While our homes are larger and somewhat unique, and your expectations should be lower with more of a cookie-cutter 4 or 5 bedroom, our gross rents average 4-5x the mortgage payment or so. 

I don’t object to starting with a house hack and moving on to a fix & flip later, and vise versaI am open to all opinions/thoughts/advice/concerns/questions to hear and really get my mind going.

Everything has already happened and cannot be changed.On the other hand, if you are a political scientist, an engineer, an architect, a musician, and yes, an investor, your success is a function of recognizing a number of different inputs, and a number of different objectives, and synthesizing them together into a working environment.You can't apply deconstruction to investing.

Sounds like Jill's advice is geared towards a business where you will be advertising your services, and you want people to know your business name, that could be good advice depending on your objective.