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). 

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?

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

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

Starting at $250 does sound like a solid starting point, might try different seasonal promotions and see what works best. 

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.

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.  

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.  

Are there any other “cover my ***” pieces i need to have?