This helps get me a look at average nightly rates, average and medium occupancy, see any seasonal changes, and lets me compare different size units along with amenities offered by top listings.

Do some people have some different stories how they bought properties in some non-traditional ways?

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

If I want to call that “investment”, comparing to 2% bank CD, then it should deliver 10K net, which is min18K with all the expenses.

SHOULD I use the equity as leverage to invest in another property or should I just go through a traditional mortgage to buy the 2nd piece of property?

For those not from the Bay Area, I was chatting with my banker the other day just comparing the "craziness" now vs 2004-ish.

Interview several so that you can compare before making a final decision and good synergy is a must!

I firmly believe in this deal but if they’re out I need to go a more traditional route.

Comparing the NY & FL markets you also have other elements like heating and snow removal which usually fall on the landlord. 

My husband did it the non-traditional way too!