Thought I would post my solution for those who may be interested.
MAIL:
I decided that having 4 addresses consolidated into gmail using labels to organize was not the best solution.....way too cumbersome. Instead, I did the following:
My two hotmail accounts-I forwarded one to the other. Then I found a great site that allowed me to turn my hotmail account into a POP3 account, which in turn allowed me to access it via gmail:
Hack to Enable Hotmail POP3 and SMTP Support Instantly for All Countries » My Digital Life
I then used this advice to combine my sent items between my two hotmail accounts, then load them into my gmail account:
Import Your Hotmail Messages into Gmail
Now my gmail grabs my hotmail, and the process works fast enough for my tastes. I set up my gmail to be able to send mail as my hotmail ids.
For my personal business account, which is through worldclient, I just set it up via BIS.
For my work account, I set that up via BIS since we do use Outlook Web Access.....I wanted to avoid having to leave my computer on 24/7 and we don't have BES at my organization.
CONTACTS AND CALENDAR:
I have google sync for for my phone to my gmail account, which works great back and forth. As far as the calendar goes, I also downloaded google calendar sync to my desktop to one way sync my from my work computer to my personal gmail account. The calendar works flawlessly thus far.
My contacts were all in hotmail. I combined the two of them since hotmail is actually pretty useful (moreso than google from what I can tell) for finding duplicates and merging them. Once I got them cleaned up I put them back into google contacts and synced everything back up.
I STILL HAVEN'T FIGURED OUT THE BEST WAY TO ACCESS AND UTILIZE THE GLOBAL ADDRESS LIST FROM MY WORK ACCOUNT, so.......if anyone can help with that it would be much appreciated!