These are professionals with additional training and a stricter code of ethics.

If there's less than 20% equity, investors might want an additional discount to make up for the additional risk.

Quote from @Brett Deas: What is everyones biggest struggle with the current mid-term listing sites (furnished finders, Airbnb etc.)? 

Additionally, if the property needs renovation, you may have a tough time finding a HML willing to lend on it in 2nd position if it is in a distressed state. 

Additionally, unrelated business income tax (UBIT) might apply if your property is financed.One option to consider is partnering funds from multiple accounts or other individuals to share in the investment, which may avoid the need for difficult-to-secure non-recourse financing.

The target rate I often see on syndication sites is around 15-18% IRR (and sometimes higher for new development projects).

It's always been my investment thesis to thread the needle of a place where a lot of people go but is not top of mind for rich people to own a second home.I like National Parks or Nat'l park sites that get 1M+ visitors per year but are not the big ones (Yosemite, Yellowstone, Zion, Grand Canyon, etc.) and have a median home price below the national average.

Buying a house, renting out the additional bedrooms at about $1000 a month on average.

They filled out an inquiry form on a listing site that mentioned their desired move-in date. 

This could manifest itself in additional damages and financial losses when they decide they don't want to put up with you any more.Also, Section 8 does require more work setting up, renewing, increasing rent, etc.