Should I jump in the pool or stay on the sidelines?

[Rick Smitts]

31 Year Old Mortgage Professional in Phoenix/Scottsdale area in Arizona. Income is good right now (500k+) but in the mortgage business as you all know can be very volatile so I am paranoid about being house rich and not having enough cash. I am a cash guy at heart and I feel comfortable having ample reserves but I dont want to be too conservative. 

 I have 100k in cash savings to invest plus the amount I need to I feel comfortable that in the event I lose my job or the mortgage industry and housing market suffers a 2008 esque crash I am still OK.. Fears I have are probably fears other investors might share. Are we at possibly the top of the market? Something has to give at some point since housing and stocks are up for last 10 years. Is it in 12 months, 36 months, 5 years? We dont know. But I fear I will get burned as many did, but I also fear sitting on the sidelines and not taking the chance to earn long term wealth. 

I am renting the home i live in. Still 12 months left on lease technically but landlord is flexible with me leaving early or even renewing lease again for another 12 months. Current rent is 2450.  This is includes down payment, repairs, furniture, etc..

Do I buy a primary residence to live in? Do I keep myself flexible and keep renting and purchase a home to rent out either as Airbnb? Do I buy a primary first, and as long as my income continues I keep saving another 100k to then buy a rental? 

Price is flexible but I would like to stay around 500k or less. I would like to be in the Scottsdale or North Phoenix Area.

Thoughts everyone?