I learned a lot through trial and error, and just being a moron half the time, but learning from my mistakes! 

Make no mistake. 

Most notably a rehab that went $100k over budget and a failed attempt at Airbnbing an Airstream that was a $30k mistake 

That's a huge mistake.

Between now and then you can really crunch the numbers on rent vs. costs and decide how much negative you can stomach....at worst you still decide to sell in the spring and maybe it's a $40K loss instead of your current estimate. 

Increase the rent for each on a worst case scenario (You know: the tenants that realize that not paying for heat means they can leave the windows open in the winter and not paying for water will never get a leaky faucet reported.

I made that mistake once, the calls wouldn't stop for months.

You can buy a lot of real estate and it's hard to make mistakes if you have the right team in place. 

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.PM us if you’d like to discuss this logical approach in greater detail!

I live in the SF Bay Area and have decided to buy my first single-family home.I fully acknowledge and recognize that the SF Bay Area and California (in general) may have some of the worst cash flow numbers in the entire country.I've already traveled to cheaper Midwestern states to look at real estate opportunities, but have decided to invest here in the SF Bay Area as I'm purchasing with the intention of living in it first and foremost, and then renting it out sometime in the near future when I move overseas.I'm looking for anywhere in the Greater Bay Area/Northern California region (even Sacramento & Central Valley is okay) with better than average purchase price to rent ratio, and some appreciation (if possible).