I have a "roommates" in residence to safeguard my interests so the property earns just enough income to cover all the costs. 

check out Safeguard properties.

Thanks everyone for such a great community.One question I have is:I have heard people talk about how often in a booming market, you'll have tons of over-leveraged investors who, when there is a big crash, they go bankrupt.How do you safeguard against this kind of thing?

Costly factors when purchasing a  property, especially a buy and hold, are unforeseen costs, especially those that could have been avoided. For example: roofing, sewer, boiler, furnace, fire safety, foundation stabili...

and was looking for all the possible pitfalls I should expect as well as all the possible safeguards I should insist on.

With that said, I would put safeguards in the deal in favor of the investor such as preferred returns. 

If you establish the plan with a qualified custodian that offers self-directed Solo(k) plans, you will have them as a safeguard for compliance purposes.By the way, the advantage of a Solo(k) plan over a self-directed IRA is that Solo(k) plans are not subject to unrelated debt financed income tax.

I set up mine with Brian Eastman of Safeguard Advisors.

When you’re done reading his posts, tell me if you didn’t “hear” him preach about losing one’s proverbial shirt IF the PROPER due diligence and safe guards aren’t set in place.I’ve thrown down the gauntlet pal.

I would be interested to know as well, how to execute and safeguard your interests in these kind of deals.A lot of guru's preach Lease option strategies but I really don't have the trust in them and their preaching.