Not realizing I was only getting a few hundred a month from it and from a cash-on-cash perspective I'd have been better off buying TBills with the click of a button instead of all the hard work, stress, time, and planning I put into it. 

Please share any helpful resources, your personal experiences, and what you have found to be valuable with every transaction.

I can say my personal experience has been pretty mediocre.

Of course, he is free to come here and prove me wrong.

Start with BiggerPockets Ultimate Beginners Guide (free).

Start with BiggerPockets Ultimate Beginners Guide (free).

But it seems like 'nothing' comes for free.  

I took a break from school and shed all points of stress in my life.

@Jonathan Blanco, I'm and investor and a licensed mortgage broker so I've been on both sides of this conversation.I would look for a lender that (1) listens to you and understands your strategy and needs (hint: it's not always money), (2) has experience working with clients executing your strategy and brings more to the table than just cash - be it advice, relationships, deal-team partners, etc., (3) gives you viable options and explains the pros and cons of each option and (4) you enjoy interacting with - this should be a relationship, not a transaction.Once you find a few lenders like this (and you should have relationships with more than one), then you can start comparing rates and fees.

In my experience, a large percentage of them are fully functional adults that refuse to take personal responsibility for their lives, which is why they are receiving free rent from taxpayers instead of working for a living.