For anyone else that may be wondering out how to do this, I've resolved it myself. It's really quite simple but only when you aren't trying to think of a difficult way around it. Basically what I did was look at the path:
http://localhost/alecu/Log/tabid/93/post/this-is-another/Default.aspx
And realized it was already a product of a FriendlyURL rewrite. So inside of the Host Settings I turned off FriendlyURLs and then revisited the blog page and received the following:
http://localhost/Default.aspx?tabid=93&post=this-is-another
Now that I knew what it looked like (what the querystrings where) I could easily rewrite it as it needed to be, which ended up like this through the backend (Host Settings->Advanced Settings->Add new rule):
MATCH: [^?]*/blog/post/(.+)
REPLACE: ~/Default.aspx?TabId=93&post=$1
I left the TabID as 93 since that is the TabID of my blog module. I then added a second rule following that with:
MATCH: [^?]*/blog/(.*)
REPLACE: ~/Default.aspx?TabId=93
Which will replace any redirect /blog with anything after it that isn't a post to this page. Admin side editing still uses standard DNN. The last bit was to change the ASCX file to generate the new format URLs (this URL for TabId/93 and normal style for anything else). I know this is probably trivial and not news for many of you, and for those of you who have already paid for a solution it is completely irrelevant. Hopefully it helps lead someone down the right track if, like me, they were having a difficult time with a simple chore.
Kevin