I only employ sub-contractors that are insured.  

If it's a decent property operating at a 7% cap you could probably take another $5-8k a year in cashflow which push returns on investment into the low 20% range....and that's on a pretty marginal property.Next year I'm selling off the rest of my personally-held stocks, the only thing left in that market will be my employer funded 401k.  

Im self employed for 3 years and doing very well.

If not, you're adding the self employment taxes and paying 40%.  

Obviously the concern is the economy and oil prices to keep him employed at this level but I digress.  

Assuming I land a job, how will that gap in my employment history affect my chances of getting a loan?  

@Kevin Lillenberg In a nutshell you may qualify to open a self-directed solo 401k if you are self-employed.

Unfortunately, I went through a tough divorce and loss of employment (was a university professor for 8 years) so my credit really tanked.

Years before FHFA argued Fannie Mae was not federal by virtue that it was private before, making FHFA act as a private entity, not the other way around, so that they could win an employment termination case where the woman claimed Fannie Mae was Federal since being held in a FHFA conservatory and thus must follow federal employment law.

Hi,I would request letters of recommendation from their employer and other sources, and have your property manager speak with each source.