I can do it myself but would rather avoid risk if possible?

Anything other than that and you risk incorrect and/or outdated info. 

Another possible strategy that lowers the risk but also lowers the rewards is to keep your existing property and rent a house in Milpitas.

You also bought a single family home instead of a multi family to spread the risk. 

I’ve talked to an agent and he literally kept trying to stear me into the direction of getting a condo or a townhouse and I’m not 100% sold on going that route being that there is more risk with roommate tension and higher vacancy issues.Thanks

If there aren't many people interested in the property, a wholesaler would have to consider an offer that has an inspection contingency otherwise they risk holding the property longer than they anticipated.However, if you're in a hot market (and who isn't these days), you may be competing with people who are willing to go after the property so aggressively that they drop all contingencies; this would represent less risk to the wholesaler of the buyer backing out so naturally they would likely choose this offer over yours with contingencies.If you're finding that all deals you're coming across do not allow contingencies, it may be valuable to spend some time learning how to expertly predict repair costs on your own so you can determine if a deal is a good one without paying for inspections before getting it under contract. 

I was taken aback recently when the tenant (1 year) asked me to seriously consider selling my house to him using an owner carry contract. 

You could form a Joint Venture Specific LLC and have a good real estate attorney draft an iron-clad Operating Agreement to minimize your risks, limit liability, and protect your personal assets all at once.

Remember your time is worth something and you are taking the risk.  

Maybe, spread the risk.