Also, I do fly a lot from Chicago OHare, especially international direct flights.

Internal Revenue Service (IRS):- https://www.irs.gov/individuals/how-do-you-report-suspected-...5.

Could you imagine the hell that would wreak on international markets!

For a property placed in service in mid-November, you can claim approximately 1.5 months of depreciation for the first year.With a cost segregation study, components may use different conventions:1.

Quote from @Hannah Tate: All, I am looking for some advice from anyone who has had experience investing in short term vacation rentals internationally.

Be respectful to these people but do not internalize their words.

This strategy identifies components of the property that can be depreciated over shorter timeframes (e.g., 5, 7, or 15 years instead of the standard 27.5 or 39 years).

Quote from @Jon Taylor: @Pete Harper - Section 721 of the Internal Revenue Code allows an investor to exchange property held for investment or business purposes for shares in a Real Estate Investment Trust (REIT) without triggering a taxable event.

It has Roth component and traditional built in.  

Also, keep in mind that some lender may have overlays that are more restrictive than the FNMA/HUD guidelines, meaning the lender's internal condo guidelines require more than FNMA/HUD.