Would that work for a triplex that you could then say you have 2/3 capital gains exemption?

I also still had my old NY state license and car registration so I had to switch those to SC, pay the car property tax, license fee, and plate fee before I could apply for my 4% property tax exemption.

If you've owned it less than 12 months, it's short-term capital gains; longer than 12 months (but less than 24 months), it's long-term capital gains.Now, if you are selling for a reason that the IRS provides an exemption, you might get away with paying gains on less than the full profit amount (you may be able to prorate as a portion of the 24 month requirement). 

Homestead is exempt, so are there non-exempt assets?

He might not even owe any gift tax if he has not used his lifetime exemption amount of around 22M right now.

Why have it if industry is exempted from it?

The guy lost a law suit and he's trying to dump it before the liens fly in beyond exemptions.

But after he moves, the first option to me would be to get him to owner finance it for a bit of cash flow for him and less taxes due to him (may not affect him if the price isn’t high or if his primary residence exemption may fully cover him).

Under a lease agreement would I not be exempt from taxes, insurance, management (I would do myself), maintenance (I don't own the property) etc...?

Your transfer may be exempt from transfer taxes if you are the sole owner of the LLC (a spouse is ok).