LLC's separate your personal assets from your investments and offer you protection from lawsuits related to your property, they can help to establish a more professional image if you plan to expand, and they provide some flexibility on how you are taxed.There are some drawbacks, included fees and administrative work, but it's ultimately best to consider speaking with a CPA to determine the best option for you. 

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.

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

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.

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.

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

Illinois REIA was established in 2015.

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.

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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.