Set up a contracts account at both Lowes and HD. 

Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

There are other loan products available that are still a low down payment. 

The license doesn't cost more, the service and quality does.And a note on that cost, in my experience hiring contractors, only a small percentage of the cost savings was due to finding the right guy who is willing to work for less.

It depends on your financial strength, the quality of the property, how many properties you own, etc.I like to start with one significant expense and three months of vacancy.

Everybody thinks they can paint because they can - you get a brush or a roller, a can of paint at Lowe's and away you go.

Long wait but I got a lot of upgrades for a very low price.

Even if I were to rent it out on Airbnb, the cash-on-cash return isn't very attractive.Specifically, I’m concerned about:High mortgage payments and the financial strain it could cause if the property doesn't generate sufficient cash flow.Cash-on-cash return is low, even with high-revenue short-term rentals.My Questions:Risk Mitigation:Any strategies I can use to mitigate the risks associated with owning a high-value property with a large mortgage?

You will learn the cost of maintenance/cap ex and how tenant quality plays a big role.  

Yes they suck. ...alot lol.Nice south bay burbs are still highly desirable, low DOM, naturally appreciate and coupled with value add still present good returns.Ironically techies (from many different cultures) still want a 3/2 picket fence house.This strategy, however, comes at great personal discomfort.