I have dealt with these vacation towns a few times and some places are already zoned in our favor. 

Quote from @Bill Brandt: Sounds like your agent didn't do you any favors. 

Government involvement in this case is actually favored, at least for me. 

If you have a good credit score and a stable income, you may be able to secure favorable loan terms.

You want to ensure that your lender is doing their upfront due diligence on the deal, has programs to get the deal done if the final numbers come in different(low DSCR requirements, favorable rent guidelines, etc), and is offering you excellent customer service.

In my experience the Landlord / Tenant laws are less favorable in Chicago and I have concerns in how the budget deficit in Illinois is going to play out.

It has not gone in my favor and is taking up the entire useful part of my lot that I am stuck owning and paying taxes on because it is tied to a mortgage on a MFH that I own.

As long as their is demand and other favorable factors in that city, if it's worth pursuing if numbers make sense. 

Therefore the property types that are the most favorable to generate bonus depreciation will be those with a high degree of what the tax code refers to as "land improvements".

That said, we don't need to be next to family but being somewhat close by has advantages so those places are favored somewhat.The strategy is to buy, househack a value-add multifamily for 2 years then rinse and repeat until we can build up enough capital to either start developing, move to larger multifamily or the wife wants to start a senior care facility.