However based on these experiences still seem too risky versus just going after some of the options with RealCrowd that seem attractive and proven. 

Like Jay said, there can be more flexibility in repayment options. 

There are towns that are not too far where there could be some options for you, but I would start going to real estate investor meetups and pair that with books and podcasts.

(Auctions and foreclosures can also provide great leads.)With $20K, hard money loans are a practical option, as they emphasize a property’s ARV over your financial history.

Make sure you research multiple options to see what fits best for your real estate goals. good luck!

Offer aid and housing options if you're able -- don't try to profit. 

What’s your vision for your next property - do you see yourself leaning towards value-add projects, or are you focusing more on turnkey options?

The original post leaves the door open for a challenge by the IRS, so the safe harbor of holding it for investment for two full years is the safer option.  

Additionally, regarding the legal structure, an LLC seems to be the most suitable option for our situation.

Some, like ours, focus on offering optional services such as renters insurance or washer/dryer rentals without requiring tenants to opt into a full package.When choosing a property manager, I recommend asking about the structure and purpose of any fees.