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Debt free is great, but you are missing out on some great tax advantages, especially if you bank, not to have payments on some type of real estate. Interest and depreciation can really help reduce your taxable income.
My house is paid for, but it came at the cost of me totally remodeling it myself. (1.5 years of work) I do have plenty of leveraged secured debt on investment properties, but in all cases I have at least 25% + in equity through improving the property or large down payments.
I used to be big into stocks and I still do invest quite large % into a roth ira, but I have given up actively managing it myself. I found out quick that I am not a wall street guru. I prefer real estate investing in my local town, where I can physically see what my investment is doing. I will give you it can be a pain in the neck dealing with tenants, but just part of the job.
My plan is to keep upgrading my primary residence every 2 years or so and buy properties that can gain significant appreciation through remodeling. Therefore I can bypass the capital gains tax.
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