If you know how to use Microsoft Word then you can figure it out pretty easily.

Obviously I could turn to investors but that seems less profitable and easily introduces potential competition.

For example, if you rent a large 2,000 sq ft house for $1,000/mo in Texas, you will incur operating expense which could easily EXCEED $500/mo.

Even with 20% down, you should be able to buy about $2,500,000 worth of property which could easily provide $4,000 per month if you buy correctly.

And how's that going to happen very easily?

Prices could easily come down significantly over the next few years and take a decade or more after that to return to present values, adjusted for inflation.

I recently moved to Top Producer Websites to allow me to get MLS search and lead generation connectivity easily.

.$30k increase over 5 years is easily justifiable in my opinion.

Should I reinvest it all along with what I started out with, or do I pay off some personal debts to reduce my overhead, so that life on irregular pay becomes more easily manageable (I would still have what I started out with to keep investing) ?

I'd think you could eliminate that by shopping down there and have a lot lower expenses.