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'm a digital marketer and investor that has helped several agents dominate their markets and then grow to have their own brokerage.A few things I noticed between the successful and unsuccessful brokers are:The successful brokers found a niche whether by location, housing type, or by client type (i.e. they only work with investors like those on BP; really the best niche because investors don't usually need hand holding and we don't care what a place looks like.)They work with agents that also pick a niche.

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

I was just in a big East coast city last week were I would say on price points under about 100k that wholesalers dominate the transactions  Now my program allows said wholesaler to close on the house and not flip the contract so they can maximize their return since its so competitive in these markets. 

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.