@Andy ThaoBay area home prices are heavily coorelated with stock price, and I expect some sort of pull back of stock price soon... hence the wait 

Someone getting into REI using the STR to create a positive cashflow can only expect (2) as a natural result, not only from the community taking action against businesses operating in residential neighborhoods, but also economic reversals where the travel industry takes a hit.BTW: Tourism has been with us since the automobile and communities thrived a long time before the advent  of STRs.The NIMBY principle is heavily at work on this subject and historically, has been effective and successful in managing change.  

It's going to heavily depend on the exact location of the property.

Very little appreciation and heavily tied to oil/gas economy. 

There are some nicer multifamily units, but not many.If you are considering multifamily here, also consider the town and region are heavily dependent on the oil and gas sector. 

I am unsure how to start and which direction to go in as I rely heavily on my current income.

Not trying to come across entitled here...I know how hard it is to get these numbers anywhere.Obviously goals affect the answer: I'm looking to finish replacing my day job salary with RE monthly income within the next 3 years, then scale up more conservatively (slant more heavily toward performing notes?) 

Half of it is also heavily wooded - The back half.

Sure thing.I'm actually a full time attorney that focuses his practice heavily on real estate.

I am focused on multi-family properties and have been studying and researching the industry very heavily over the past couple of months.