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?

Prioritize your financial stability.

For a while I looked into medium size deals like 30-50 units in class B neighborhoods, but ultimately could not negotiate a deal to the point where it would have made financial sense.

@Derick JenningsRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Be a long-term investor focusing on controlling as many assets as possible most safely. 

-------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Commercial based assets rely on NOI and cap rates to compute value.

i say that not to discourage you, but so that you have a realistic picture of what to expect.as @Travis Timmons alluded to, you need to be in a strong financial position to even think about starting to invest. 

Prioritize your financial stability.

NEVER INVEST MORE THAN 10% OF YOUR INVESTABLE ASSETS IN ANY ONE DEAL.