Say you start a STR and use the loophole to write off 100k from W2 salary. 2 yrs later the rental goes underwater and you have to give it up at huge loss.  

You quantify losses due to withdrawing your 401k - then you leave the real estate investing completely vague.

You found a new tenant immediately, so there's no financial loss to you except for the time spent marketing, screening, etc. 

You still cannot benefit from pass through depreciation and carry forward losses to offset tax liabilities from their active source of income. 

TIA.I track rates by following:https://www.walkerdunlop.com/funding-your-vision/financing-o...These are Freddie Mac rates which will be better than what you can get elsewhere, but it will give you an idea of how much rates have moved recently. 

Every time it was handled differently  LOLIt should still be up to 25% (it could be less if your marginal bracket was less, but its not in your OP).Incidentally, you can offset the depreciation recapture with capital losses.  

When there is a storm, the entire state sucks up the losses by raising premiums.

-If the person dies later than expected, I face a financial loss. 

Zoning is an important first set to to look at to make sure your vision is actually allowed on the land.

the property with the most 3-5 year stuff should be on your short list to sell now if you're cash-strapped and you can at least cut your loss without having to inject more cash.