Does Google consider a webmaster's history as a ranking factor too?

Here is the deal:

I own some websites where I admittedly did a lot of "bad stuff" in the past with blog networks etc...years ago.

Those websites have been slapped into oblivion and their link profile is also really bad. (Before I got slapped, the sites were #1 for many years, but this was before Penguin). However, I never really got a msg on webmaster tools but I have a strong reason to believe that one of the sites was manually ranked down)

One of the sites had only about 20 articles on it and I figured I don't even bother with "repairing" the link-profile etc, I simply re-make the entire site.

So I got a new domain and I am now redoing the entire site, writing new quality content. Starting from scratch without any shady techniques.

Now I am unsure whether I should add the site to webmaster tools and/or put analytics on it. The old site I still have. (It is so bad penalized that I cannot even find the articles on Google even with the articles being unique...ironically it ranks beautifully on other search engines still).

I am afraid that Google sees that I am the owner of BOTH sites and this may affect my potential rankings. I am also afraid that somehow my history is taken into account as a ranking factor.

On the other hand I feel like a fool because the site now is very good (imho) with nice content etc...so I don't know why I shouldn't put the site into webmaster tools since I don't see a reason to "hide" from Google.

The same concerns I have when I want to bookmark or link to it, say, from facebook etc...because obviously I used my facebook/twitter in the past also to promote the old, "bad" site. Am I just paranoid and should I just focus on the quality of my new site and the quality of my links?

(One factor here is that I think that *if* Google is interested in the identity and history of a site owner there will be many ways anyway to find this out, eg. IP adress, WHOIS, cookies, etc..so in other words the attempt to "hide" is foolish anyway because practically it's nearly impossible. For instance, most of the time I am logged into my Google account etc...)