Even though there are multiple variables to assess here, what's the age of the property? 

I definitely think with your age and the money you have, I would look into a vacation type area that has STRs.

And what is a "mileage book" anyway in the age of navigation apps?

One of the biggest pitfalls is the age of the buildings I'm looking at. 

It wasn't a good deal $90k because of the age, weird layout, and the bathroom was tiny. 

When I was his age and even into my early 30's I had a fear of speaking to people or publicly and am comfortable doing it now, but we have felt this is a good skill to have.

The other thing to consider is the age and if you add a second floor will the entire structure need to be brought up to code for hurricane and wind.I live in a neighborhood where the homes are older (not in florida) and the foundations are hollow core CMU and adding a second floor would not be feasible due to soil bearing.

Hell I can get an aged SHELF (not shell) company for $695 there and it was the EIN and all that. 

Perhaps you're more bothered by by our anti-guru sentiment, and not our anti-note sentiment?

What I would do today knowing what I know and based on my age (im 54 now).