I know flipping is going to come with its own set of stressors, but I feel comfortable in that realm, because in my day job I basically do Fix & Flip projects but for commercial HVAC.

The answer to your question is heavily dependent on multiple factors such as being a good manager of things generally speaking, how well you do your tenant screening, how comfortable you are with bookkeeping (if you are going to do it yourself), if you have a good selection of service providers in the area etc. 

Are there resources for an average Joe in figuring out how to maximize the revenue for an opportunity like this?

If it really weighs on you so much and you want to police the activities of your tenants, just honestly tell him that you're not comfortable and demand an explanation.

You can throw some paint on this and let it go for a while, that's up to your comfort level....

For the BP sheet, you can click on Advanced and set your annual increase amounts for rents & value.Down payment will depend on:1) What reserves you feel comfortable with2) How aggressive you plan to be on your next purchase.

The buyer just needs to be comfortable that there are no pending liabilities, and it will have to be a cash buyer.

Although the San Diego market is competitive with low inventory and high demand, I see abundant opportunity to maximize real estate investments by employing creative strategies.

Looking for some options to maximize cash out on a refi where the SFH is in owned by an LLC. 

You could also attempt to look up their phone number and cold call if you're comfortable with such.