David Crook's article on getting started as a real estate investor for The Wall Street Journal provides some good ideas on getting started conservatively in real estate investment.
An important nuance I'd like to point out about the article, though, has to do with second homes vs. rentals.
While you may get more favorable tax treatment when buying a property as a rental as opposed to a second home, your mortgage lender will charge you a premium if you request a loan for an investment property.
You need to understand what that premium is and understand how that compares to the benefits of favorable tax treatment.
When you consult with an appropriate professional familiar with your situation, be sure to ask about the different legal structures you can use to hold your property and gain asset protection as well as tax advantages.
Nonetheless, the experience you'll get with some of David Crook's ideas like renting out your in-law unit and taking a "buy-and-hold" approach to property investment will help you overcome much of the fear associated with getting into real estate.