Are there any good general guidelines for evaluating the relative attractiveness of an STR for the so-called Loophole strategy to shelter W2 income?   

However, for the first time, I started looking into it about a month ago and I found that there's a thing called short-term tax strategies—not really a loophole, but that's what people call it.

However, for the first time, I started looking into it about a month ago and I found that there's a thing called short-term tax strategies—not really a loophole, but that's what people call it.

@Amy Houghton The STR tax loophole generally does not apply to midterm rentals which are typically leased for 30 days or more.

After hearing about this STR Loophole, I reached out to my tax preparer to see if she was aware of this. 

Loopholes are something UNintended.

I appreciate your attempt at educating folks with your post, but personally it really bothers me when people keep referring to what is in the tax law as loopholes.

That means cost segregation and bonus depreciation are already available, and those deductions can offset other income if the owner materially participates (already similar to the "STR loophole").

That time frame also prepares buyer in case they need to have a certain reserve requirement or gift funds.There are also some tricks and loopholes that can make or break the transition and the timeline.

With a property manager, you often lose access to the short-term rental tax loophole, which is one of the major perks of STRs.