The way you are describing your Investment idea, reminds me of beginner Stock Investors.

I recently just finished college but am a avid investor in the stock market.

Though I personally can't speak on the CA market (other than that A LOT of your fellow Californians are in the same spot as you), Wes always has great input, so I trust his analysis.I also think you should heed the advice of @Yousif Abudra, especially regarding determining your goals (cashflow vs appreciation) and narrowing your field of focus.

But the biggest help is it helps me become an area expert, making it easier to spot good deals.  

A person walking on the roof will add a significant amount of weight to one small spot, increasing the risk of structural failure and personal injury.

I have a lot of money invested in the stock market, and I'm doing pretty well, but I know the party may be coming to end, so I'm looking at alternatives.  

@Raymond Wu  First off, I'm licensed in a different state, under different laws, so take the advice I'm giving in consideration of your local laws.Basically, you're in a really tough spot on this.

But to simply give up an asset to save tax that you wouldn't necessarily have to pay anyway seems shortsighted.This is where scenario 3 comes into play.Your exit strategies are pretty spot on. 

I've got my eye on Canandaigua, Farmington and Victor as potential meeting spots and will keep you posted.

Hi @Chinmay J.Wayne is spot on.