I think the "short term loophole" is probably a great way for tax benefits for my situation, just not sure if I'd be ready to commit to something more active like that.

steps to decide: 1-flush out the cash flows & sales proceeds of both scenarios, discount them based on what % of the return is likely to be realized vs "optimistic"2-find a delta in the cash flow of the risk-adjusted outcomes (pretend these are your most-likely outcomes)3-determine your time investment on the self-managed opportunity4-divide line item 2 by line item 3 and compare against how much income per year / hour your time is roughly worth5-if this figure is less than your desired income, avoid the time commitment investment; and if the figure is more than your income, buy the time commitment if you're wiling to do it.

For some people, buying is not a financial option; others may just not want to be committed to a mortgage.

@John McConnell I've been thinking about it for a couple of years but never really moved due to my job commitments.  

But, being committed to my family and financial freedom fueled my “Why”.

Remember that like most of these sites, the data may be stale.It depends on the seller whether they want no financing contingencies or if they're flexible.It depends on whether you can get the info a lender would need to go in to closing with a loan commitment.

I don't have the time to commit in studying the case law tonight but I can see how one would orchestrate an 11 year rental with the intent to flip. 

I personally have 2 years left on my commitment.

Invest in yourself and commit! 

I would view this as the ideal situation,  as a month to month does not commit anyone long term, but I  manage myself.