Ideally looking to be oceanfront or close to it with purchase price less than 500k, with the goal of having a "house hack" seasonal vacation rental for seniors or company extended stay sort of thing which would pay mortgage, taxes and HOA.  

I'll make that my goal.

Yes, this can be a huge time saver especially if your jurisdiction considers this an "addition" instead of a "new construction" which generally makes it easier and faster to get a permit.

For example, reduce my ROI goals slightly to account for a higher offer to be made.On one hand, I just keep making offers with the numbers that work for me and eventually I'll get a bite.  

Understanding your end goal and building a plan to achieving it is far more important than the idea or thought of just buying one property. 

I would encourage you to be as transparent with the seller as possible as your goal should be to help them out of a situation albeit tax delinquency, code violations, divorce, foreclosure etc... 

My goal is to be financially free and independent within 5 years and working just for fun so I don't get bored and into trouble. 

Not exactly sure where I will be after that time period, most likely closer to LA (family, friends, gf, all live in LA) My initial goal was to "house hack" a duplex, but after some looking on redfin/trulia, it seems almost impossible to do with the amount I got preapproved with.

This process tends to be quicker and the goal is to buy and then turn around and sell as fast as possible. 

I'm passionate about real estate pros building relationships with designers who help accomplish business goals rather than just create a good-looking design.