pfsense + squidcache or Windows + webcache

[#1]

Hi guys..
Im after opinions off u linux guys which route to go..  Im going  to be setting up a hardware firewall , + a webcache setup but wondering do i go linux or windows route..
Im want to load balance my new internet connections ( 3 in total ) and i know i can do this within pfsense but Im not very tech savy with pfsense, Mainly due to not being arsed to learn a new os and sticking with microsuck windoze program due to it being easier.
I'll also be looking at using Squidcache also ( due to the kids ) as many vids on youtube seems to make it look like a good setup.. again my linux skills are pretty much nothing. and it takes 2 mins to setup on windows.
I'm also going to be setting up my old web site ( apache ) yet again i know i can run this from pfsense however my old site is still setup on my windoze box ( win 7 x64 ) but it like to run it all from one box keeping costs down
And lets not forget having a firewall in front of all this .. yet again Pfsense comes to the rescue. - or stick with a corprate firewall or something alike .
The only thing ill be adding to the setup which will be 100% ran by windoze  is my file server which is already setup and running.

Any  ideas??
cheers

[#2]

Personally I wouldn't want the web facing server on the same box as the primary firewall, but otherwise yes pfSense can run Squid (I actually use for a HTTPS proxy that I use for machines that need to connect to untrusted wifi - By that i mean a proxy that the browser connects to using HTTPS, not a proxy for HTTPS sites)
It also makes installing it quite easy, you goto packages > squid3 and hit install then you have to do some basic config via the web interface and voilla one squid proxy.
Just be aware for proxying HTTPS connections you either need to have it set as an explicit proxy or you need to Man in the middle attack the SSL traffic which will cause certificate errors on the connected devices unless they trust the proxies certificate and you will have to MITM the SSL traffic if you want to cache the https content.
This is one of the things that's irritating me about the sudden push for everything to go HTTPS, it breaks most web-caches and there is a lot of stuff on the internet that really doesn't need to be served securely unless people really are that paranoid that someones interested in which cat videos they watch 

[#3]

LOL cat videos   
well i have 3 pcs sitting around, c2d e84004gb ram,  Q66008gb ram, and a q9300,32GBit ram  ( ftp/ file server )  so i can always run a seperate Pfsense box  rarther than having the website on the same setup..
just thinking , do i use pfsense or a windoze subtitue due to ease of use...  + when something goes wrong i can usally sort the problem out right away but on pfsense / linux i wouldnt have a clue really.
All this https on a linux box makes me wanna hide.  ...  On;y so i can watch cat videos on my mobile lol

[#4]

Why not use one of the other firewall appliances?
I used to run Smoothwall, features on a minitx box when I was still on Adsl and had M$ pc's.
Snort, web caching etc, plugins to add features. All controlled via html internally.
But there are others available