@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.

These vehicles aren't going to tie your assets to a single family property.In no way do I think TKs are a bad thing, I think they are great options for some people and a win-win for investors and TK operators.

I haven't sold a vehicle yet but would be willing to sell a vehicle and have at the least $2500 to put a down payment on it.

I would be interested in establishing other investment vehicles independently through my own business, separate and apart from my current employer.