With winter coming would you be able to re-rent the place quick and easy? 

A general rule that works in my market at least is if inventory is less than 6 months, it's a sellers market and prices will be higher, the opposite is true of over six months.

@Himanshu JainIt all depends on how aggressive the board is with rentals and it sounds like this Association sticks to the rules. 

It doesn't quite meet the 50% rule but I'm paying it off in 15 years instead of 30 and I could always re-fi or get a HELOC to get some of my cash out if a major expense like a roof or something popped up. 

You might want to narrow your scope, because it's easy to get overwhelmed if you try to learn about everything.Welcome to the site.

I contacted NASB / www.iralending.com - and they seem pretty easy to work with.  

Quickly realizing that it is very expensive to live out here, so it challenging to find properties that would pass the rule of thumb tests (50%, 2% rules, etc).

Other than that easy peasy.

The 1% or 2% rule applies to when you're doing a quick evaluation to see if BUYING a property for an investment makes it worthwhile.

House hacking is also an awesome strategy in CA because you get to lock in low property tax rates and it is relatively easy to cash out the equity you build in a primary residence and use it to leverage your next property.