Hi Dan, I have been an airbnb host in Chicago (Lakeview and Gold Coast) for three years and have found it to be great supplemental income.

If you run your business in an ethical, BUSINESS-LIKE manner your odds of getting involved in a lawsuit are pretty darn slim.I would suggest that a much better investment would be to explore taking a few BUSINESS AND CONTRACT LAW classes at your local University, and supplement that with a REAL ESTATE LAW class that's in conformance with the Continuing and Professional Education standard for RE Agents in your state.The purposes of these classes is NOT to turn you into a lawyer, but it's like the Law classes generally taken by Business majors and MBA candidates in Universities; to teach you WHEN TO CALL A LAWYER.all cash

There is no one size fits all method, there's no real wrong answers, as long as one is committed to doing the things necessary to improve their life, I believe real estate can supplement any goal or lifestyle.

The income from the multi-family would be enough to save, maintain, and modestly supplement my income.

I use my rentals as a way to propel and supplement my passions. 

Also keep in mind that the cost of life insurance is going up every year and eventually premiums that you are paying are not enough to cover the cost of the insurance, at that time funds from your savings component are used to supplement the cost of insurance.

In addition, supplementing my RE education with in person seminars definitely can't hurt (as long as they aren't $300 a pop).

You can also sell on contract, via a wrap note, using a note if you own free and clear, etc.I think the purest form of buy-and-hold investors generally intend to hold the property indefinitely to produce cash to supplement or replace their income.

I'm thinking of investing for cash flow to supplement their monthly income.

I am supplementing this loss with bombing the biggest hills on my bike I can find around here.I almost bought my first property in Hermosa with a former co-worker.