I think an important piece to note is you will not end up at the same destination with both approaches.

You'll figure out more questions as you talk with other agents and brokers.One last piece of advice, its not the end of the world to change brokerages later (beware, some to many brokers seem to take this personally). 

If you know of any that could assist with promoting our distinctive offering effectively, your recommendation would be invaluable.

Setting this up is only one piece.

Maybe the "classification" isn't the important piece - but can I write off expenses if I occupy a property more than 14 days?

He also sent me 3 pictures of some small pieces of trash left in the ROW and told me to go pick them up.

Same goes when acting as the buyer's agent.This is three separate and distinct business transactions. not one.

One of the single most important pieces of advice that I have ever received is that Timing the Market doesn't work, however, Time In the market does.  

IT IS GOING TO BE THE MOST EXPENSIVE PIECE OF EDUCATION THAT YOU WILL NEVER PAID, 12 weeks of pre recorded, obsolete and bad quality training for $20k-$50k.

You'd likely be better off with 1 small multifamily here in san diego for 900k to $1.3M range vs 10 single family homes in a random market at 100k a piece.