As such, you may not create a transaction where there is any direct or indirect benefit in either direction between yourself (or a LLC you own, which is still you) and your 401(k).While there is theory that you and your plan can "very separately joint-venture" into a transaction, it would be very easy for the IRS to find holes in your transaction that create some form of benefit. 

Purchase price: $214,000 Cash invested: $3,500 Took a single family home and converted basement into separate unit.

The fact that you also have separate W-2 income should not prevent your self-employment activity from sponsoring a retirement plan.  

Instead of 5 separate houses with 5 roofs to maintain, etc, you only worry about one roof over everyone.

I’m thinking about house hacking for the first time with an FHA loan 3.5% down.There’s a duplex that someone is selling me off market at $220k in a very good area in Tampa, FL (West Tampa is the area). 2/1 each unit and the rents are usually $950-$1,000, separate electric meters, one water meter.

The two properties are sold together for $900,000 or separately for a total of at least $800,000.Option 4: My parents sell the house for the $500,000 estimated value. 

I’m just not so positive how it being 2 separate duplex’s would pan out?

However, there is a good reason to have them wired separately (see my next bullet point)

If I go the route of pursuing 4 separate properties, I would try to close just 2 properties within the 180-day window.

Accumulate tax-sheltered savings separately in your employer plan.