Ensure that your cash flow needs are met, and you have a diversified income stream to support your retirement lifestyle.In conclusion, your decision should be based on a comprehensive analysis of your financial goals, risk tolerance, and market research.

Could we buy a property > $500k a year out of college with two streams of income?

In the basement I hung streams of toilet paper....and when the room is still, no heat flowing - I notice the toilet paper swaying a little bit.

So in theory you need to have multiple passive stream that generate losses and you accumulate it over the years.

If you have other income streams that you can personally strengthen it's likely best to focus on those streams while continuing to invest in professionally managed BIG deals!  

I would get rid of the rest and convert them into a steady income streams.

Yes, hurricanes can be worrisome, some much more than others, but with a reliable insurance policy, I have a hard time believing you will find a US beach market outside of the Gulf Coast that provides a more reliable income stream for at least 6, usually 8, months out of the year.

That additional 80K you have on hand can be used to purchase another investment property = another stream of income + portfolio expansion.  

Additionally, the potential for value-add opportunities such as adding a ministorage or other high cap rate investments in the future could further increase the overall return on investment.Considering the potential for appreciation, the current NOI, and the future potential for additional income streams, this property could be worth considering as a long-term investment, despite the initial lower cash on cash return.

They aren't going to let a perfectly good vrbo income stream sit idle for long.Alternatively, you could try to find the house on various websites such as AirDNA, which should give you a rough approximation of what the property has historically earned.