I heard a podcast that mentioned an established vacation market in Michigan.

@Laura Williams that is a great question and I failed to mention it.

As mentioned in the other post, deciding what your true goal is as well will help you choose a market.

As mentioned in the podcast, you can carry forward the paper loss, which could offset future rental income or other income once the property is fully operational as a rental.To maximize your benefit, doing the cost segregation study now while bonus depreciation is still at 100% would allow you to accelerate depreciation and take advantage of the full deduction in the year the property is placed in service as a rental.

If the building is currently recognized as a single family residence,  then you are changing use and presumably will need to sprinkler the building and satisfy other fire rating and STC rating requirements not to mention the added costs of having to run mechanicals for multiple units, multiple kitchens, additional bathrooms etc.  

I would not be surprised if this was a very well thought out plan that someone would move to another country that could avoid everything you mentioned while living there where ex pats are welcome and can live a wonderful life. 

Aside from the Debt-to-income ratio and risk benefits you've already mentioned, it also just helps keep everything organized.

And as for Track Record, as both Chris and Brian mention: this is important to see.  

-your first few years after a purchase are typically a stabilization period, and you IN-vesting your money into the property. think about how long it will take to recoup all the costs i just mentioned.

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.