Loosing cold cash

This idea that biking is cheap and fun is taking a bit of a blow with the cooler winds and more work on the bike. At the same time I feel more disconnected without riding in to school.
First reconsider the costs. It is costing more than predicted, but I'm not too worried yet. I didn't need to buy a bike, but there's been plenty of maintenance that has been deferred over twenty years, and some things will only need to be dealt with once. This past week I've replaced my chain and the freewheel (gears in the back). It was easier than I thought, I followed the advice at Bicycle Tutor. It still needed a chain (out of stock at Nashbar apparently when I ordered the last big box.) a chain tool, a free wheel remover in addition to the chain and new gears. Now I'm reading, and Gary at SouthCoast cycling is telling me chains only last for about 1000 miles. Need to measure at 1000 miles anyway. This is insane. The chain is $20 or so from the local bike shop, cheaper on line but there's shipping. The bike sounded much quieter with the new chain and gears, but it felt the same (even had a slip once) and I didn't go any faster. Other purchases have been for rain and cold weather (helmet cover, full finger gloves) and more visibility (back light - the planet bike blinky). I'm leaving well before the sun rise, its clear and dim stars are visible (the sublime views must be worth some cash - consider how much we spend on telescopes). The vest, helmet cover and leg straps are all "specialized" bike gear and reflective. I still may want to rethink some clothes (wool tights?) as I was both cold and sweaty this morning, a complete strike out. Currently I have "fancy" long john shirt, a t shirt then the fuzzy and a vest. The thought was that any sweat would get pulled away (it was) where it would be able to vent out (it didn't).
Other purchases include a floor pump, a cone wrench to try to get the brakes held tight but not stuck, a spoke wrench (the wheels had begun to wobble) and a cycle computer (not yet installed, to see if I could improve my time somewhat). Finally I decided to replace the rear tire (not original, but old and worn) with fancy "all condition" armadillo tires from Tri-Town cycling. Only got one to try it out. So far its not popped out (mentioned on line as a problem with putting them on old wheel rims).
The graph that compares the amount saved to the amount spent is not closing fast (at the time of this post about $80 gained, $490 spent). I expect that the "newness" of the task has blown up the cost a bit. Thoreau wrote to beware of all new enterprises that require new clothes. He has a point, I'm easy prey for catalogs or articles promising more comfort in cool weather as it is pretty cold. I want to be visible. Where will it end? I see more winter gear(some booties would be nice), better panniers, new wheels to replace the corroded ones I have now looming in the year ahead.
I also feel a rush to get home and haven't ridden on days that require a project after school. This means there has been two weeks with only one day of riding. I am not too embarrassed to be a fair weather cyclist. Any day is better than none. I had hoped for at least two days a week. The average for one month is only 1.5 per week. Only managed to break 500 miles in October (was thinking it would be about a month's worth). Only 339 in September (mostly commuting) we'll hope for more in October.