This would be my first foray into real estate investing... and I absolutely 100% agree that the best move is to establish a track record using my own money and conventional loans before considering using private money.

Eliminate debt, establish a budget, and save.

Within the U.S. if you want to avoid the bureaucratic nightmares that often follow STRs you will probably want to invest in a well established STR market that already has laws favorable to STRs.

I was fortunate enough to live in Detroit for several years, so I was able to establish a network before moving back to California.

Illinois REIA was established in 2015.

@Mindy Jensen this is what I do until I've established a good relationship with them. 

It's also worth noting that, given my community development background, the intent is to help them refi into traditional financing after they've established a payment history.

If, a year from now, you have an extra $20k piled up because you have been serious about this, it established a bit of a track record and proves that you are a doer and not just a dreamer.I would also express gratitude that you have a partner that is so cautious.

(Further context on the role, the business has solid marketing and network established.

You could even consider a condo with an established HOA that’s STR-friendly—it can simplify maintenance and management.A Few Other Things to Note: Documentation is everything.