Cold Weather Cycling - FAIL

Went out for a group ride this morning and only made it about 5 miles (22 minutes) the headed back.  We headed south for about 1 mile.  No issues here.  Starting to warm my core up.  Now we head west and into the 18-24 mph wind.  I only lasted about 4 miles before I had to turn back.  Seems like everything was against me and nothing for me.

What I did wrong:

1. My toes went numb and the skin on the fronts of my ankles were exposed and getting windburned.  I need to purchase thermal shoe covers and possibly wool cycling socks ($5 - $30).
2. My fingers went numb.  I was wearing full finger gloves but they were not wind proof.  I need to purchase a pair of windproof thermal gloves ($10 - $100).
3. My water bottle was filled with ice and water so by the time I needed a sip the contents were solid enough I could not squeeze the bottle ( I did not fill the bottle myself).  Fill bottles with plain tap water ($0).
4. My legs were starting to get really cold on the ride back.  I was wearing a pair of light weight running/warm-up pants with cycling bibs underneath.  I need to purchase a pair of thermal tights/bibs ($50 - $120).
5. I was wearing 2 thermal long sleeve shirts so my core was warm.  Maybe too warm.  I was also wearing a rather loose wind/rain proof jacket.  I need to purchase an appropriate cycling specific wind/rain proof jacket ($50 - $100).

What I did right:

1. I wore a balaclava under my helmet.  This protected my neck and ears from the wind and cold ($5 - $30).

Summary:  

My head and core was comfortable.  My fingers toes and legs were hurting.  It is end of the cold season here in Illinois so I will keep my eye out for sales on cold weather cycling gear primarily for my hands, feet and legs otherwise I'll catch is again next season.

I finished my ride with a total of 10.35 miles in 44 minutes.  Average speed of 13.8 on my Trek 7.5 fx hybrid bike.