You might also want to explore specialized banks that focus on working with high-net-worth individuals who leverage insurance products like Merrill Lynch Private Banking or Wells Fargo’s Private Banking division.

(Sorry all the tax professionals that responded, I know you are better at this than your average consumer)Is there a way to ballpark how much bonus depreciation I may even be able to use as a tax loss to offset income?

You can call local banks typically credit unions in the area to see if they have a construction loan product.

I now make it a habit to set clear expectations with lenders upfront and ask about their average response time

This can go so many ways.The last people you want to talk to is a normal, average financial advisor.

With used cars averaging $34,859 and full-coverage insurance costing $2,496 annually, only California is pricier.

The WORST solution is an unqualified attorney, because their mistakes makes whatever they come up with INFERIOR to an “off the shelf” solution.In between the two we have a good off the shelf product by a reputable vendor.  

Under this rule, if your average stay is seven days or less and you materially participate in managing the property, you can treat it as non-passive income and potentially use tax losses (like depreciation) to offset other income.

This will provide a roughly 10% nominal return likely over the next few decades as it has averaged that since 1900.He says it's simple and other than his son Howard, the others have little interest in investing/finance, and the sp500 index has outperformed >98% of professional money managers over any 20yr or greater stretch. 

Property taxes and insurance have gone up on average of $100 year after year.