Wasted time is infinitely more expensive than not getting it right the first time around.You must keep going through tough times.

If I didn't provide high end top shelf linens I'd be out of business before I started. 

Cash is infinitely versatile.Tax-wise, paying the principal down and recasting will be nearly identical.

I live and rent in Manhattan, and for the first time in 20 years there are a few vacancies in my building . however , in upstate New York , where I invest , homes are flying off the shelf - people are bidding above asking.

The junk that was FLYING off the shelf in May is sitting and being reduced.What you say could very well be true and will will know by DEC.

This may be a basic question, but I’m considering moving my reserves for my three properties into a whole life insurance policy, eg Infinite banking.

My dad isn't an attorney, but he knows infinitely more about the law than your average joe.

I want to have money come flowing to me without me having to go trade my time for it.So, naturally, the potentially infinite streams of revenue from real estate, constantly coming in, checks every month, are very appealing!

You can't bring these guys a set of plans, you have to pick their off the shelf models. 

@Natalie Kolodij and @Jake Hottenrott, the issue here is that if a property's average period of customer use is 7 days or less (as many if not most Airbnbs are though I'm not sure about @Sara Erickson's case), it's not considered a rental activity under Reg §1.469-1T(e)(3)(ii)(A) and therefore would not be depreciated under 27.5 years, which is reserved for residential rental property under §168.That being said, the scope of Reg §1.469-1T(e)(3)(ii) limits the scope of Reg §1.469-1T(e)(3)(ii)(A) to the 7-day-or-less rule to Reg §1.469-1T(e)(3), not §168 and not the entire IRC.And of course the regs for the 7-day-or-less rule are temporary regs issued in 2002, and the shelf life on temporary regs is 3 years.But nevertheless these regs probably give some insight into Treasury's thought process here.Speaking of which...Airbnb wasn't a thing in 2002, and Treasury's presumption back then may have been that the "rental" of a property with an average period of customer use of 7 days or less would likely have been bundled with some significant services, thus making the entire activity a trade or business rather than a rental.But things are different now, though obviously some services are provided with the typical Airbnb (e.g., the provision of clean sheets, television, complimentary snacks, etc.) that aren't provided in the typical rental...What do I do?