it's a real gamble, especially right now with so much demand driving auctions up.

It seems like a big gamble to guess at which option is more secure.

My concern is making it so complicated through land trusts, LLC's, offshore holding companies, and C corps that our accountants can't follow it and our bankers won't loan to us because they don't understand our corporate structure.  

If the second unit does not have its own electric meter it should still work (worked for us,  we bought a home with attached apartment with our daughter who was a college student) also if the appraiser classifies the second unit as an accessory apartment or mother in law unit or casita instead of calling it a "duplex"   We're taking a gamble on a property right now where the underwriter said he believes the appraiser will be classify it as a single family with accessory unit (fingers crossed) this property is two separate homes with separate meters, so there's a chance appraiser will say the dreaded "duplex" and we wont qualify. 

The possibility of an error that could cost tens of thousands is not worth gambling.  

I'm willing to accept some risk, but I'm not going to gamble.

That’s called gambling my friend.

just think of off shore scammers that do the IRS stuff  and any number of other scams these guys can hook up.. like the guys from India or Bangladesh that claim to be IRS officers with a super thick accent but a name of Jim Smith  LOL.. 

It was a huge gamble because I had never invested in Miami before, let alone out of state at all.

ANd they say appreciation is gambling  LOL.. great job great gambles perfect timing all the star's aligned congrats !