How can I structure a deal with a local agent in my area so that I can access the MLS to not only seek out deals but evaluate market conditions?

If you feel it is still a good deal with cash flow of $500/month go for it but be ware managing a PM will be a work in progress, they often require a lot of work to get the right one trained.

Multi in many markets is very frothy.no different here in PDX.however when you go to other markets with higher returns your risking the tenant base.. so be careful there if you think that's your next progression.

By documenting to your contractor in clear, sharp detail your desires, they will be able to make field decisions on the fly without disrupting progress.

The three options you offer can not be evaluated with out know all the details of the property.

Until that attitude changes, you're unlikely to make much progress getting the average real estate investor to diversify--especially into stock/mutual funds/ETFs (Buy and hold?

Furthermore, with mls access and realtor only information for property evaluation, it is extremely valuable when picking properties and negotiating prices.

@Michelle Damiano I recommend that you get some education on evaluating and buying notes before you pull that trigger.

It is used as one way to evaluate financial performance. 

You cannot evaluate someone's work when you are not qualified to do so.