The other thing I meant to mention with EV in CA. and I am not sure if its this way in the Bay Area on 880 or 101 or 280 or 680 but the HOV lanes in LA if you have an EV you can run in the HOV lane with one person..

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

you mention ARV - what is the cost to repair the property to get it to that ARV?

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.

-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.

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.  

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

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.

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.