Tier 2, 1 and $$ questions

I have about 5 individual tier 2 web 2.0's that point to my Tier 1 web-site. My tier 1 web-site is just 1 blog with some content and a few links to my $$ web-site. I Was thinking lately if it would benefit me If I started posting additinal blogs on my tier 1 everyday and pointing to other landing pages on my $$ site, or will that start leaving bad footprints?

That is a very good strategy and make sure that you build tiers to those additional tier one properties you are building.

You'll not leave a footprint if you follow that and you should get some nice linkjuice to your site that way.