Thanks for the info about your area ! 

So if I offer $100-150 off first months rent and get someone in there sooner, it actually saves me.

I cant tell you how many amendments we have had to do for clients who wanted to do it themselves and lost 5 figures + in tax savings 

The guy does put out great content, but as always, they put out just enough info to sucker you in and then take you to the bank to get the rest.

Some helpful info on knowing how DSCR rates and guidelines broadly work: DSCR loans won't use your income to underwrite the loan. 

But my understanding is also that there can be tremendous tax benefits / write offs when it comes to real-estate.I am looking for more guidance from professionals on how to structure my investments and how I could potentially harness the power of depreciation and write-offs to legally save money on my active earned income.

I have resources, stats, contacts, and further info available on any of the above.

Find an agent that actually knows a bit about investments and can help you get info such as rental estimates and after-renovations value

The paths available seem to be one of three (1) work at something producing more income than needed to live and save aggressively to acquire capital.

So, dig in and see if you can do a reasonable repair and get several more years out of that roof allowing you to save and budget for a replacement at a time of your choosing. 2.