Howard Said:

Payoff everything in 5 years or continue to build real estate portfolio?

We Answered:

You are definitely on the right track, but I would erase all debt except for your primary residence and "vacation home", as there are significant tax advantages to this debt over others. The rental property interest should be tax deductible as a business expense. When everything else is paid off, you can use the equity in those properties to get money more easily if the real estate market has improved. If it hasn't, you will have more money to look at properties that would be even cheaper than today.
With the glut of property out there, make sure you have enough savings to carry the property without income for at least 6 months to a year, in case the real estate market continues to deteriorate. It would be a shame to have come this far, but lose it all in 5 years because you overextended now.