And in 2013 SF already surpassed it previous highs, and now is at record values.

Even doing all the work yourself it is easy to surpass that in materials especially if you need a roof or anything major. 

Will Newark live up to the hype in surpassing Hoboken as a desirable neighborhood to live in?

Go make your first deal and the amount of knowledge you'll gain from just that will far surpass anything you've read.

If you want commercial retail you might work on fixing your credit and showing good income on your tax returns.Then find a retail condo unit you could possibly buy for 100k to 200k to get started.Regular commercial  the closing costs alone will surpass the 15k to 20k you are saving up.Takes a lot of money to do commercial. 

Is your theory that the market would be so inundated with turnkey rentals that it would surpass the need for quality rentals?

I just read in the newspaper yesterday that RU generates an economic impact of more than $1 billion annually to the area, and I'm sure that VT surpasses that.

I have embraced debt to grow, and it has worked, but now I am getting a little jittery as I have surpassed my ability to repay the debts from other income.  

There will always be a market for a hipster looking to save a few bucks to invest in their extra curricular substance activities :)     If you really believe supply could surpass demand simply reach out to the university. they have the data available as to how much student housing is available in a geographic area around the university.  

There will always be someone who has done something better than you and as such, once you keep up with and surpass Mr. or Mrs.