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We plan to conduct a cost segregation study to help increase the tax advantages.

Situation:-NOT a REP (don't qualify and a STR doesn't make sense because I'm in a VHCOL area -- numbers just don't work)-purchase a property (eg, $1,000,000)-conduct a cost segregation study on it (eg, $500k accelerated, the rest is land and/or on a standard schedule)-rent out property for 1-2 years-sell property after 2 years, but you have not utilized all the bonus deprecation, say you have $400k left you've been carryingNow my understanding is that I can utilize that $400k carryover to offset "active income" (eg, w2, interests, dividends, capital gains and ROTH conversions).

Throughout my career, I have consistently conducted business with integrity, transparency, and the utmost professionalism.

They always conduct their own due diligence to ensure everything is accurate and we usually have an in-depth dialogue with them regarding the financials prior to filing. 

None of what I said here really can qualify as advice as I have not seen any of the specifics of your tax situation but you really need a strategist to get in there and (1) help determine if REPS is even the right path for you or if there are better strategies available to you, (2) help provide taxable income projections so that you understand your tax liability given varying scenarios, and (3) help you conduct the strategy so that you are "audit ready" in the event that you are audited in the future.

We would need more facts to conduct a proper post-mortem on this to share any insight.

We self manage our rental property and was wondering if there is an inspection service that helps conduct quarterly inspection of the property?

A buyer may have an obligation to conduct reasonable due diligence and explore any indicia that his seller may not have title to the property, including exclusive possession.  

Don't forget you need the original developer's permission to conduct structural changes to the villa inside and out.