The pro's is its predictable but the downside is the interest is typically calculated month to month so any early payment or payments prior to the start of the new month (usually the 1st of the next month) do not lower your daily interest cost.

Flipping a house, even if Dennis does 2-3 a year, still takes months to complete plus if he has a home office in which he runs the flips from and researches for new property all while taking the tax deduction for it, is all running a business and i would be very careful playing that gameAgreed, this is a highly subjective fact intensive determination and border line cases are notoriously difficult to predict, with selected outcomes at times being contrary to what one would expect.

In addition, landlords receive a ResidentScore, which is a score that is specifically for the rental industry (15% better at predicting eviction risk than a typical credit score).

Let's start with stocks, there isn't a big secret there the best strategy is buy and hold, not trying to day trade and predict trendlines, invest in a broad index fund with low fees and wait, that's pretty much all there is to it there.  

Medium term too many things out of your control to predict so don't bother, just be ready to ride it out if you need to. 

If not, sell and reinvest in a Class A or B property where they tenants will be more predictable.

Whereas, insurance is less predictable.

It's less about which is better and more about setting a solid foundation for creating consistency and predictability in your lead flow. 

While the market here has stabilized and things are looking better it is impossible to predict. 

The biggest issue for me now is finding time while forking a day job in NYC with a hour commute each way.OTOH, if by the time your are 65+ you may be just totally fed up with this business and want to cash out and hopefully by this time you have built up a good amount of equity in your investments if you bought right and managed right you should be in a great position to cash out and find truly passive investments if that's what you desireIt's also hard to predict how one will feel 15 20 years into the future.