Not a lawyer so no legal advice, just a question:  Wouldn't filing for bankruptcy protection enable you to keep your primary residence and also possibly have the courts help you to go back on monthly payments for your tax debt? 

This will enable you to accomplish more in a shorter period of time than if you rely on just yourself.

I would ideally like to transition fully into real estate investing in the next year, possibly by supplementing with a few traditional real estate deals once I pass my real estate licensing exam and get sponsored by a broker.

At some point you should have achieved those BIGGERpockets that will now enable you to use your own cash to invest.The housing market is doing well now. 

Your money is growing at 100% per year and you could (again, theoretically) just keep adding more capital to enable he team to do more flips:  Year 1: $60KYear 2: $120KYear 3: $240K Year 4: $460KYear 5: $920KYear 6: $1.8MMSo let's take this extrapolation and create a better marketing pitch:"INVEST $30K WITH ME AND WE WILL RETURN NEARLY $2 MILLION DOLLARS TO YOU AT THE END OF 6 YEARS!"

If you just want a half a dozen free-and-clear rental properties to supplement your retirement income, then pay them off (especially if deals are hard to come by or the numbers don't make sense).There are many people on BP that haven't been in the real estate game long enough to have weathered the 2007-2008 storm with substantial real estate holdings, so be leery of taking advice from these people when it comes to risk and leverage.  

If it's a hot market, I generally would take the following approach:Offer whatever the seller is asking so you can tie it up as soon as possible, SO long as (1) the list price is within $5k of what I will close them for.... and (2) the price you offer minus $5K will be a purchase price that will enable you to achieve your target returnI know that I will negotiate the price down after inspection and most sellers are unwilling to drop the price more than $5K after inspection unless something is seriously wrong with the property. 

Filing of paper tax returns will remain available after that date.IRS Modernized e-file, the system that processes electronically-filed individual returns, will shut down after Nov. 18 so the agency can perform annual maintenance and to enable the IRS to reprogram the system for the upcoming 2018 tax-filing season.As a result, any taxpayer needing to file after Nov. 18 will need to do so on paper.While most individuals have already filed their 2016 federal tax returns, certain taxpayers may qualify for an extension until Jan. 31, 2018.

Like anyone, I am just wanting to leave as little capital in the properties as possible thus enabling me to obtain more properties quickly. 

It sounds like a good program and will enable me to fill other vacancies in the future.