The deal will involve complicated paperwork. 

However, even in an equal exchange, recapture tax might apply.

Hi Aaron,It's always challenging when companies go through transitions like this, especially when it involves something as personal and critical as managing retirement accounts.

Build a solid foundation before taking a step up - each and every step of the way.There’s a way to scale recklessly and there is a way to scale safely.When OPM is involved safe is way better than reckless.Despite a life long career in RE, I scaled as followsBought a few duplexes for my own accountBought a fourplex for my own accountBought 12 units as a JV with some friendsSyndicated 43 unitsSyndicated 30 unitsBought another 12 units as a JVSyndicated 281 unitsThis was over a 3 or 4 year period.and so forth - now I am GP in close to 1000 units with $125M AUM.Even with all that, my sweet spot is 30 to 50 unit properties - they work best for my partners and I and more importantly our investors. 

Courses and webinars are great if you're getting basic information to help start you off, but you'll never truly retain the information if you don't apply it.

I'm involved in too many things, but that's what happens when you have a family and kids to support.

Be very careful who you take advice from online, you should get involved with a local attorney and a local realtor.

@Anthony Sigala that "Rule" was created for mostly Class B properties BEFORE the Great RE Crash of 2008-2010.Values after the Crash dropped so much, that it could also be used for Class A rentals.Values are now more than their pre-crash highs, so the rule now only applies to Class B & C rentals.How are you identifying Class B & C submarkets in your area, so you can properly apply the rule to the right rentals?

From the beginning of the discussions though Buncombe County has said that the regulations will only apply to STR owners who apply for a permit after the application window closes, meaning that you should have nothing to worry about if you buy soon enough and then apply for the grandfathering during the window of opportunity.

The capital stack especially in CA is VERY complex and typically involves everything and more that you mentioned.