Yes he does if they're properly categorized as employees and not ICs or owners... 

Some lenders will do a HELOC in first position (recorded as the only mortgage) I’ve been told.  

You're accelerating your education by constantly putting yourself in position to talk to people with problems, much faster, and on a much more consistent basis.  

I know notice is needed to access the dwelling. 

I know that between 3 and 6 months before the redemption period expires, I must serve all parties with a final take notice that requires that I inform them that a petition for a tax deed has been filed and the court date for that hearing.

It's at 13.59% interest rate that would equate to $296 in monthly payments - this would take away any positive cash flow. 

A real gem.I now want to work on my passive income so I can leave my soul sucking factory job to persue other business ventures.I’m in a good position to have this work out well either way I choose to proceed but I’m looking for some advice from those of you who have been in the game for a while.

@Tarik Nabi I don't think you can take a position that getting rid of rodents is the tenant's responsibility. 

@Chace Fraser I do like the sound of that "Rich Dad Poor Dad" approach although house hacking might leave me little positive cash flow unless I get a killer deal quadruplex.

So if this will be his 5th year of not paying taxes, the county should start that process after he doesn’t pay and he’ll begin to get some notices in the mail which could help with his motivation.