We could possible both be able to acquire two properties <500k with FHA with the caveats of being in a market further from Boston, being required to live in one of the units (unless we commit mortgage fraud- not recommended I hear), and having lower cash flow since we'd be living in one of the units instead of collecting rent.

Ok, I see, but I would guess that this could trigger an audit of your ownership.I took a quick look to learn about the Florida homestead exemption and there is a TON of info about fraud in the system.

Further, you will be subject to the numerous and various fraud, securities and trade laws should you be sued by a disgruntled investor.Forty some years ago the SEC decided to rectify this situation by creating a well defined private offering exemption from registration offering option known by to rule numbers Regulation D 504, 505 and 506. 506(b) became most popular, 506(c) was added to accommodate internet offerings about 6 years ago.The gist of compliance with Reg D is the issuance of a private placement memorandum, the acceptance of only accredited investors as investors, disclosure requirements, and the filing of a Reg D form with the SEC, as well as notification filings with the individual states where the investors reside.The cost of the Reg D all in, mostly legal and filing fees, ranges from $10,000 to $25,000.

Personally I am betting it's a complete fraud, but like I said, entertainment value, curious how ridiculous this will all get. 

Purchase price: $118,175 Cash invested: $26,900 I have moved out of my first duplex I was house hacking after purchasing another almost identical duplex on the same decommissioned air force base.

Too many investors jump straight to this step resulting in homeowners getting a bunch of nearly identical yellow letters that offer nothing unique that will get that owner to actually call.If you take nothing else away from this long post, please know that the unique value you bring to the owner, and how good your are at explaining that to them (the message) is FAR MORE IMPORTANT then the list you choose.

I travel back and forth overseas throughout the months sporadically at months at a time which is why I feel like trying to make it my primary residence would fall under occupancy fraud?

The HUD changes were specifically meant (check their wording) to address the flagrant fraud involved in the whole ESA scam, and to make the requirements harsher, in fact stating that an online letter, by itself, is not adequate to establish the right for an ESA.Reasons a Landlord can deny an ESA:1) It causes a financial burden2) It causes a potentially dangerous situation3) It causes a hardship to neighbors4) The building is 4 units or less and the landlord lives there5) The property is a SFH rented without the use of an agent6) The ESA has caused significant property damage in the past7) Insufficient or fraudulent documentation is provided8) Illegal breedsHere is a good, fair site for info devoted to landlords: https://landlordgurus.com/emot...

I will say that right now, contractor fraud is a huge topic in Pensacola and 2x contractors were put in jail for it.

All of these docs and the license info should have the identical business address.