It's relatively easy to look at comparable properties on airbnb with the same bed/bath, general condition, and location and click around their calendar to get a sense of what they're making in bookings each month.

You can 1031 exchange a portion that makes sense for you (office right now is market specific and an opportunity if you know what you're doing), and take the other portion as "BOOT" and pay taxes on that portion. 

I'm trying to stay level-headed and unemotional about it (it's not going to kill my deal regardless), but this doesn't pass the common sense test.  

Yes I think that makes the most sense too. 

Set your goals, take a conservative approach, trust the data, and if it doesn’t make sense, don’t do it.

People seriously please stop spreading complete non-sense around, because the people new to this WILL believe your crap and you are ruining their lives!

Hey @Sima MehBuying a property with a mice problem and possible mold can be worthwhile if the numbers make sense.

The return on investment just doesn't make sense sometimes in the short term.

At the metrics it had when I bought it just didn’t make sense.

I am not fully familiar with the San Jose market, but if they only allow 180 days of STR, then the other 6 months being a MTR would make the most sense.