Your idea of having a different business model (mid-term for corporate people) is in the same vein and is a great one but I wonder how big that market is given the structure of the economy in Punta Cana.

I've had great success this year by purchasing the company (LLC or Corporation) that holds the property rather than buying the property directly.

I spent 15 years in corporate sales, but was tired of having a traditional boss and got myself into a solid financial position to be able to do so without taking on the stress of a commission-only career (as someone with a wife, a mortgage, and two kids). 

Since filing separate tax returns could increase your taxes, a "post nuptial agreement" would allow you to still file jointly but distinguish the properties for your other situation.

Filing jointly just makes this messy.

Yes, you should file asap or you really have nothing (anyone can file before you) - Cure!!! 

Their quoted fee: $5,000 — and that’s just for the strategy itself, not actually filing the taxes.For context: I do not file my own taxes.

In one he checked the box on the application that said he or no entity he was involved with had ever file for bankruptcy.

Now I'm in a LOT of debt and everyone around me has been telling me to file bankruptcy.

Was this a Reg D filing?