If you get a lot of properties it would be fun to have the first tab pulling data for metrics on portfolio performance, monthly cash flow, expenses, etc.

Louisiana is also a very landlord friendly state and that doesn't hurt either.I have been looking at the rental data in New Orleans lately and it seems like there may be a surplus of rentals available, most likely due to the STR rules causing people to switch to regular long-term rentals.

You need to learn to be an expert in some source of stress at finding, filtering for (a data source tool like propstream.com) or buying from a data vender who is good. 

I joined Bigger Pockets in the hopes to connect with like minded individuals who would like to mentor and or just overall help one another so that everyone can be confident and achieve the best possible outcome as we embark on this Journey of investing. 

Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

Is anyone using Stessa and importing Airbnb transactions into Stessa? Works really well (I used the CSV option) - but the Stessa import tool does not bring in the GUEST SERVICE FEE from the Airbnb transaction. Any ide...

Then after that is achieved, we will begin saving for a down payment on our first house that we plan to buy in the next 2-4 years.

Partner Driven saw the Benton St property as an opportunity to achieve a high return with minimal initial investment, focusing on its high potential in the Pleasant Hill market.

High rent growth areas are likely to achieve positive cash flow quicker than low rent growth areas.  5 years for cash flow seems reasonable in many markets.  

You should really analyze your options, as data should make your decision easier:)How much have you been making on the STR?