Starting Out Huge, 1.45M Investment Property Opportunity

[Chris Vicari]

The Basics: I've been watching the micro-climate that is San Diego's short-term vacation rental market since I moved there in 2015. I have numerous friends who rent out their primary residence and completely cover their annual costs through rental income. My work is entirely overseas for about 190 days a year. 

The Property: San Diego, 1.5 miles from Ocean Beach, established neighborhood. 3bed/3bath with detached casita income property, ~3900 square feet on 9,000 square foot lot, waterfall and pool as central feature inside primary residence, very high end finishes and priced at 1.45M, almost $200-300 less per square foot than any near comps. The ultimate bachelor pad. 

Finances: 30 y/o (newly) single male, owned 2 houses, 750 FICO, $150k cash, $100k in 401k/IRA. $170k annual gross in income and $12k annually from the VA, with no debt or payments to the ex.

The 1.5 Million Dollar Question(s): 

• Is it reasonable to expect I can cover costs and perhaps even generate a profit by renting out my home and the casita when I'm away and staying in the casita part time when I am stateside to justify such an expense? 
• Hard Money Lenders, Traditional/VA Jumbo Loan, or find a business partner that wants to invest and potentially live there with me?
• How would you go about securing financing for this?

I'm a long time reader and a first time poster, I've ran the rental calculator and determined that my costs would be around $120k annually all-in. I can't cover that without rental income but due to the uniqueness of the property, I believe I can get 60% or higher occupancy rates for a median rate of $700-900/night annually, with outliers north of $3,000/night during holidays and major events. I am aware that San Diego may vote eventually to ban rentals less than 30 days. 

I believe the property isn't set up well for families and is more closer to the playboy mansion than a traditional family home. Also, it appears to be listed grossly under market but it's difficult to comp. My house down the street is being listed at $550/sq ft and isn't even close to as awesome as this place. 

Talk me out of this, or into this. I can only see the upside in this, am I wrong here?