It's also essential to factor in your financing costs and ensure your cash flow projections align with holding costs.

But if you want to use a conservative approach and use the extra cash flow to pay off debt versus further investing, I think that's a very legitimate way to go about it.

I don't have a ton of cash right now so figuring how to do it all creatively is definitely in my priority list.

Soon there will be a refinancing event wherein I will be cashed out. 

These will catch a buyer’s eye in any market, and it's no extra material cost to do so!

Or like many small in businesses you raise cash from friends family and anyone else that knows loves and trusts you.The other thing I suggest is to make that $27,000 or $37000, or $50000 yourself over the next year. 

Researching local job markets, schools, and even infrastructure projects can provide insight into potential appreciation and cash flow.You might want to explore markets in the Midwest or South, which often have lower entry points and better cash flow potential compared to California.

I am in Madison, WI where in general think you will find good appreciation and rental demand, but higher price points and am sure less cash flow than other WI locations. 

You may also have to get your "hands dirty" in order to make these properties cash flow.

Limiting factors on purchasing the property are EM (5% on $10M is $500k of your own cash you're putting at risk), needing a net worth of guarantors to equal the loan amount and last but not least, finding enough capital who's willing to invest with a first time investor.