Real Estate) within a corporate vehicle(C Corp or S Corp).The LLC is likely the route you want to go but it should be advised to consult with an attorney and your CPA.

Funds will be coming from a combination of a Roth IRA acct, Money Market, a cash-out refi of a paid-off vehicle (about $11k), and some physical cash.2.

This may be a great learning vehicle for you.

@Peter Gill the property did pay for itself. it was 1.5 acres in the city limits so I charged companies with commercial vehicles $500 a month to store their vehicles on my lot.

Real estate is just a vehicle that can be used to reach your financial goals and someday free you from having to work for money.You do have to have money to buy real estate, but it doesn't have to be your money.

You do get tax advantages by putting it into the 401k to then purchase, but you will kill your personal cash flow from the property by using a 5 year amortized loan from your 401k to buy it.With you wanting to be FI prior to the 401k distribution age, there really isn't a reason to chuck it into the retirement vehicle first.

It all depends on the specific vehicle, much like the answer to your question depends on the specific deal.My suggestion is to not worry about it until you have a deal in front of you. 

The rent free home is over an hour from my work, so I am taking into consideration the cost of fuel/vehicle maintenance.

@Colleen Ferrari,Self-directed Solo 401k is great investment vehicle (in addition to being awesome tax-shelter), however it is not for everyone.

I am assuming that the interest rate on your student loans, vehicle, and mortgage are relatively low so you don't need to be in a HUGE rush to pay those off.