Others may have a pool of folks needing housing but don't currently possess the traditional methods to enter a home they deserve.

As a serial house hacker, my advice for your first house hack is to simplify things. 

The goal is speed + recycling capital, not hitting a “perfect product” on Day 1.A house doesn’t need to be fully modernized to get a strong appraisal, especially if structural, mechanical, and cosmetic basics are already improved.3.

Quote from @Josh Hall: The house I am about to list for rent is located in the county and trash pickup is not offered.

During COVID I made a lot of money putting used furniture in half way updated houses 30 mins from downtown. 

Let’s look at Indianapolis IN; (not my market, just using it since it is a popular place)  https://www.redfin.com/city/9170/IN/Indianapolis/housing-market for a median price of $250K That's the range you want to start out in, as a beginner.Then we assume 35% of ARV (After Repair Value) to do the rehab, holding costs, sales costs and profit.

The U.S. housing market will finally turn the corner in 2026, with a double-digit increase in home sales supporting a 4% increase in home prices, according to new predictions from the National Association of Realtors®.NAR Chief Economist Lawrence Yun forecasts sales volume for existing homes will rise 14% next year after three years of stagnation, and sees new-home sales rising 5%.

Yes I do worry about my kiddos with both house hacking and renting a room to a stranger. 

I definitely recommend starting house hacking, then look to input sweat equity for repairs to refinance or sell later

You are already on the right course with looking to house hack a small multifamily, so that's great.