Hi Whitney,
Welcome to BP! I think you should keep your options open, so to speak. Just do all of those things he expects you to do as an assistant and search for deals for him and for other investors as well. As a wholesaler, you need a long list of investors to market properties to. But you can start with a few. Also, I realized through trial and error that wholesaling is not 100% "no investment capital required" business. Almost in every deal you would need money for the escrow within 3 days, but it depends on how good you are at talking to the sellers and getting them to sign a contract with you with no deposit.
In my professional life I mostly deal with realtors who protect their clients and would not advise the seller sign a contract with no EMD (earnest money deposit), just like they would not advise the buyer to sign a "no contingencies" contract, which means if you back out for any reason you are sure to lose your EMD.
As a realtor, I find properties for my clients on the MLS, where the sellers are usually represented by other realtors. I was successful at finding a duplex for my client just a few months ago that was qualified for FHA financing. His funds to close were less than $4,000. Also, his monthly mortgage payments are completely paid by the tenant in the other unit making his housing expenses $0.
I also bought my first rental duplex last year with a private money loan that cash flows $500 every month.
Let me know if you would like to start looking for your houshacking deal. You do need to qualify with the lender by providing them your last 2 years of tax returns, w2s or 1099s, bank statements, etc. It is quite a process.
Good luck with everything!
