So I've been trying to determine where to start investing in Real Estate and have had a tough time finding particular areas to focus on as the options seem endless.

Unless you have an endless stockpile of cash, your investment strategy will stop short (especially for younger investors). 

The possibilities are endless here.

A statistical compilation of sending endless written offers is highly discouraged.

Honestly, you can just Google "Yellow letters template" and begin to make your own from the endless examples that come up. 

So I always saw myself diving into the world of construction, home remodeling, design, investing, etc. someday (also watching endless hours of HGTV as a teen definitely does something to your brain).

Technology is awesome and when you combine with real estate, there are endless possibilites.

I have been playing the game of blocking the holes with rocks, rebar, wire mesh, etc but the groundhog's patience is endless.... just digs a new hole right next to the blocked one. 

The tools, mentors and connections you can meet are endless.

Jared,   no one buys those properties to make money or have great returns, they buy them to be able to live in a neighborhood they may not otherwise be able to, or want the income to offset their housing expense. there are plenty of areas near where you live that you can find Sub $100K duplexes that get $900+ per unit. the Madison and surrounding area market is insane, hard to make a dime there unless you have endless cash sitting around with no place else to go with it.