However, once I started making good money in wholesaling/investing I did invest $30k+ in several courses, which may sound insane, but I've gotten way more than that back in tangible money, in addition to building lasting relationships and gaining TONS of extra knowledge.

Some of these sources will expose you to extra taxes.

Or if you like giving the state extra money.... :-)

If so, should I start having them pay extra per month for the event of they do leave in the future?

The danger of doing this though is that you don't know how the tenant was screened which presents extra risk.

This particular house is 600 sq ft with a full basement and potential for extra rooms.

I suspect few would not be thrilled with this ROI, but seeing it is my worse ROI I recognize I could have done better with numerous other RE Investment opportunities.  

I like to spend extra and outfit my properties with good quality.

Typically this means they will take longer to close, may not have all the information of the companies they work with, and most hard money brokers get their money by taking an existing product and adding extra points to pay their fee.

Typically this means they will take longer to close, may not have all the information of the companies they work with, and most hard money brokers get their money by taking an existing product and adding extra points to pay their fee.