The more stable the rental market, and the longer term you have tenants (who are not constantly looking for a house to buy and then moving out) the lower your cap rate will be.

My personal take:1) I have a strong personal income stream that can take the occasional need to subsidize my investments2) My goal is to focus on getting a large cash flow stream for when I want to stop or slow down working. $100-$200/mo is irrelevant to my lifestyle now (I'm very fortunate to be able to say this, and realize for many others that may not be the case).

I have been constantly learning about real estate and investing in general from BiggerPockets and YouTube since I was 15.

The idea of buying and holding real estate to provide both an immediate revenue stream and a long term investment is very enticing. 

As others have mentioned, having multiple streams of income is the true path to wealth creation.

Of course the loan programs are constantly changing, so what's best for you will depend on the rules when you go to buy, and your specific situation.In this area real estate agents should be decently experienced with VA loans.

We actually have 4 revenue streams; management, leasing, project management, and market analysis.  

As I am in the early stages of my real estate career, I also want to build a strong investment portfolio as an additional stream of income.

Should I actively seek to find a property I can "afford" now and house hack it considering I'm paying $800/mo in rent to someone else, or should I just be patient and finish my studies and then jump in with a steady income stream?

I'm a wholesaler as well and I've heard of prop stream a few times but have never used it.