Paying down debt isn't always the answer, but if the anticipated  gross return is close to equal, take the risk-free, hassle-free,  tax-free path every time. 

Here is where I began recounting my memories of my internship with the jolly excel model.This path of education and experience is more along the lines of corporate real estate, which is why I chose this over pursuing my license and residential real estate endeavors.

I would love to connect to some members of this community and hear a little more about their stories and use it as motivation to help me get where it is that I desire to go and find my path for success. 

That could be no garage (when all the other homes on the street have one), backing up to or on a busy main street, bordering or in ear shot of active railroad tracks, in airport flight paths, or where the subject property sits next to or across from a trashed house.

Sounds like you're already on the right path by being here - just keep learning and asking questions and like @Luke Trovinger said, get started!

But I'm with you, I prefer cash flow at this point in my path.

Hotels across the country are facing staffing problems, which is limiting hotel capacity and driving prices up.

Interesting path, but we all get to where we are one way or another.

If you have experience investing in this area of the country and can shed some light and insight into taxes, insurance, Airbnb options (easy/hard/impossible), permits, flooding, other potential issues, etc., I'd be most grateful!

You really can't go wrong with any of the three strategies you mentioned: house-hack, local multi-family or out of state investment property. i would suggest fine tuning your goals before choosing a path.