Without that knowledge along the way, you may miss something that someone more seasoned wouldn't. 

I think if you find a property that is close enough to the mountain, maybe off moonridge, then it should attract enough renters to offset the higher property management costs and longer vacancies like the property you stayed at.The problem is finding a property like the one you mentioned, as a property like that would be overpriced in this market, as an owner who’s selling would bake in the price of it being fully rented in a “normal” winter season.

By the time you get up and running and get your review status up, you'll miss much of the spring/summer season.

Just wondering what the market is like seasonally.

Just need to check with your lender about seasoning period. 

I understand Tahoe is a preferable market for STR (Yes, I know about Measure T :) ) due to the year round attractions with exception to the shoulder seasons, but really open to everywhere with a decent market in Norcal.

Or say, they'll fund the 90% LTV example, but client is a borderline credit case and has never owned a home (I'm a seasoned investor, with multiple properties, and I've bought and sold dozens of homes).  

I need some seasoned investor advice to help me navigate the excitement of our new venture.

The Beach condo during the seasonal events/boat races rents for $25k-$30k a month. 

Don't forget to factor in seasonality.