But given our tribe's tendency to skirt the rules and believe in the magical powers of "I will just tell the IRS..." - it's a slippery slope. 

Would we be automatically classified as real estate dealers in the eyes of the IRS for this one flip?

Whether or not it would pass with the IRS depends on language used in the agreement and the wordings in the settlement statement. 

I expect my Florida market will be hopping soon. 

You can only check on your taxes with the IRS if you know all the details of your return… some are easy enough… name, filing status, but then they also ask for the amount of tax due or maybe it’s your AGI… I forget.. but it’s nothing you will know if you don’t have a copy of your return.It’s total BS if they are going “Huh, I don’t know what’s going on.Here’s the frustrating part.  

Thanks to a special IRS tax loophole, homeowners can exclude $250,000 to $500,000 of capital gains from the sale of a primary residence, so long as they have lived in the property for two out of the prior five years."

Pace Morby is the guy i look up to the most when it comes to creative financing, and i was wondering if i could meet up, or hop on the phone with somebody who knows the game pretty well to grab some advice. 

We have 8 business entities availing of their services, and as "advisors", they should make business life easier -- not add more work on your plate --- but instead, my team and I have been checking for mistakes, or following up on action items, missed deadlines, and paying penalties to the IRS and Secretaries of State due to their negligence.

For example, if you had a full time job (2000 hours per year), you'd have to justify that you did 2001 hours doing real estate related activities.See the IRS' page regarding activities:  https://www.irs.gov/publications/p925#en_US_2022_publink1000...The other question is why are you have so much passive losses to bring onto your main 1040? 

I think another fear with going conventional is whether the house would appraise for the asking price if the orchard isn't taken into account... ir the cashflow from the two rentals.