The idea of “giving back” by providing the kind of experience you’ve appreciated as a traveler is such a fantastic approach and will definitely resonate with renters, especially healthcare professionals.Single-family homes and cabins sound like a perfect fit for what you’re envisioning.

Hey Lauren, I read you wanted to retire in NC - great choice as I believe it will also fit nicely with your plan of owing turnkey SF rental property.

You'll be tagging transactions throughout the year with categories that fit the Schedule E so when tax time comes (if you stay on top of it) every deposit and expenditure will already be categorized and it's quick to create the Schedule E and/or run P&L reports any time you need to.

We have a big place so it is families and groups.I do ask guests before booking if they are celebrating any special occasions and I will add some extra things to the welcome box that fits if I can.

Get knowledge, follow experienced people, and leverage wisely.My Take:If you have two houses, excellent credit, and motivation to build wealth, you can learn to manage your money responsibly.Use HELOC, credit cards, and business credit funding to leverage your cash and buy properties faster.

Similar areas that have legal under utilized permitted space convert to max studios that you can fit.  

Are you willing to reject several potential tenants until you find the right fit (I doubt it given how you were always talking about how busy you were)? 

Again, if the numbers work, and you can fit in the cost of a PM service, what's the holdup?

I bought a Class A (nice Indy suburban home with excellent schools) in 2013 and it's appreciated (doubled in value from 2013 to 2021) and I'm positive cash flow because of my low interest rate, 3.875%.

@Drew Sygit, thank you for the excellent reply!