I am so glad you asked this question. Here is a rambling answer.
Last year I started investing again and I started looking into real estate. I also began investing in the stock market again.
I have found out what I like about stock investing, I found a great advisory service that I have high confidence in, and I have been learning to use options for income, as well as margin buying power and protective hedges.
I sought out advice about options investing in particular because Kiyosaki says if you are going to do stocks, you had better learn options. I am learning about options with a conservative, investor's approach (not a trader's approach) and I am making income with options. It has been a GREAT experience.
Not everything has made money, but I am doing well in the big picture, and I am learning from the mistakes I've made. I actively watch the stock market and read and try to keep learning.
My income on options is looking a lot to me like income from an investment property -- I can make hundreds of dollars a month of income from tactics like sold puts and covered calls.
I also have a few nice dividend payers that might compare well (appreciation + dividends) with some of the lower cap rate properties out there.
Your danger with the stock market is if the market swings and you bail, you are locking in your losses. Your other danger is if you are buying wrong (overpriced, or a poor quality business.) Not many companies go poof!
In all honesty, I may be happier overall with stock investing vs. real estate investing, but I am still learning about real estate investing and may go there.
I am lured by the bigger returns 15%, 20%, 25%, etc. from real estate. My thinking:
If I can buy a high quality company with a 6% dividend trading near it's low with no tenants, toilets and trash, why would I bother with a low cap rate property?
So if I go for real estate, I'm going to be greedy and want the bigger returns. And maybe that is coming with much more risk. It is more of a business.
I have learned some important things in the past year.
1. With stocks, there is *no way* I would go it alone without a great advisor. My fees are not huge and I credit "my team" with helping me invest wisely and safely.
2. It takes some time to learn how you want to invest. At first I tried a service that was more high growth and high risk. It did not suit me. I later found the right fit and I feel great about where I'm going now.
3. I think it is good to jump in -- a little. I did not know exactly what I was doing with my first options trades, but practice increases understanding. I am learning and it is great, it feels good.
Last -- it is VERY possible to lose money in the stock market. Don't mess around with it. It sounds like you have a system you are happy with that is working for you. That is good.
Like with a real estate investment, don't forget your stock investments. You have to know what's going on.
I am not sure yet where my head is at with real estate investing. Based on my experience with stocks, I might be inclined to try to find a great partner to learn from. I might be inclined to focus on very high quality investments that will appreciate and cash flow.
I love the flexibility of stocks. I have the opportunity to make small mistakes that are easy to fix or undo, usually quickly and cheaply. With real estate, I hear it is "forgiving", but I am not sad about taking my time to learn and if I never start in RE, I will still be happy with stocks.
Good luck! Have fun and keep learning.
I think it may be better to focus on one or the other and get really good at one strategy. However, I do like the BP community a lot! Fun place to hang out with the RE folks!