New to BP and hoping for advice on my plan with a plot

[Aaron Andrew]

Hi everyone, I have a plot of land in the middle of Tulsa, OK that I'm hoping to sell and use to start my real estate investing journey. My goal is to own a B class property in Vancouver BC, San Diego CA, Miami FL and New York City and every 3 months, move and live in the different locations (Miami Jan-Mar then NYC April-June., Vancouver July-Sept and SD Oct-Dec). I would Airbnb the rooms when I wasn't in town.

I currently rent a place in San Diego and have a telecommuting job building websites. I estimate I'll get about $60k for the lot - it's a half acre in a nice, dense residential area. I have access to about $20K more in savings and family. What I am not sure about is:

• How do I best go about selling the lot in Tulsa?
• Is my plan crazy?
• If it isn't crazy, which city should I start with?
• Who are some folks I might want to reach out to in each city?
• What else am I missing?

And many more but I don't want to get ahead of myself.  Thanks from a huge new BP fan!

Aaron