Unfortunately the recommendations are all the same people, the aforementioned 3 builders/1 roofer/etc, like mentioned before they are absolutely not hurting for work so they are giving me astronomical prices. 

I live in NY and like many have decided to start investing however the prices here are astronomical.

Real estate prices in downtown Chicago are astronomical. 

As for the competitive aspect, I live in the Denver area and the competitiveness and cost is astronomical here. 

Neither of which are an astronomical amount, however, how often can i expect a tree root to grow through the waterline or electrical failure to surge out a fridge to justify any extra coverage that wouldn't be covered by my monthly maintenance savings?

For instance, the network one can build from going to an Ivy League school such as Harvard is priceless (the extreme end of the spectrum) to the appreciation of working with people from all over the world in a university setting (diversity breeds creativity).Though the cost of higher education in the US is astronomically high when compared to other parts of the world, the benefits should always be weighed not only on the cost but on the intangible elements of higher education. 

Probably astronomical I assume

If you compound monthly it will create an astronomical annualized interest rate. 

I'm from Long Island, New York (Suffolk county) where it is nearly impossible to start as an investor in real estate due to astronomical house prices and even higher taxes.

The risk that comes from not knowing what you are doing in a deal like this is astronomical.