The question for me is, are we better off investing that money monthly in tax free bonds,

I am of the opinion this is worse than burying cash in the back yard. Bonds can and will loose value when interest rates rise.

Last time I checked marginal income tax rates were under 100% and both capital gains are dividends got special treatment. For a period of 8 years why not look at something like Vanguard's Wellington. It has done well over just about every 8 year period since it started in the 1920s

Gordon
Atlanta