I am trying to give my car a rest and do my regular commutes on my bike. I'm trying to get my body in shape for a half ironman and figure as much time as I can get in is a good thing. the problem is of the 10 attempts I have made of the 9 mine commute, one way, only 3 of them have gone smoothly. After the first flat I started carrying a tool kit, 5 flats later, one of them a broken valve stem from my mini pump, I invested in a new foot pump and mini pump. then I had a blowout just airing the tires up, twice, so I broke down and got new tires. I thought I finally had the hardware figured out so I tried again ended up having my rear derailleur fall apart, so I got that fixed along with some other maintenance, it ended up taking a week longer and $20 more than I was originally told. when I finally got my bike back the next shift I decided to try again I hit some uneven pavement going 15mph and ended up in the trauma ward.

I'm starting to think this whole commuting thing isn't for me, or maybe my bike is actually trying to kill me. has anyone else had a learning curve like this? should I give up now before I do some real damage, or take this as another lesson and stick to it?

I smell a Wal-Mart bike... am I wrong?

If not, these are all tests of your mettle. It will get easier.

It sounds like you've had a rougher than usual introduction. It should get better. Through your own trial and error, and preferably, knowledge from this forum, you'll figure out solutions to all the issues and become a successful, seasoned commuter.
My first recommendation would be to learn how to do as much of your own maintenance as possible. This will save untold amounts of time and money. Once your bike is in good working condition, you'd be surprised how little maintenance it takes to keep it that way. Main tasks are cleaning & lubing chain; & fixing/replacing flats. Riding in wet conditions will drive chain/drivetrain maintenance requirments up considerably. Fenders will offset that to a large degree.
If it is a crapmart bike, I'd recommend that you start researching what better quality bike would meet your long-term needs. If you're serious about commuting daily, you'll be much happier with a good quality bike that doesn't introduce avoidable issues into your commuting regimen.

As far as flats go, it makes no difference if you are riding a Wally or a Pinnarello. You will go months, possibly years without one, then get a dozen in a month, often more than one a day. Learn to fix them, and practice doing it quickly.

Commuting successfully, and with the same ease and reliability as driving, requires:

1) a well-maintained quality bike,
2) equipped for how you ride and what you need to carry, and
3) some experience as a rider.

It sounds like you have either a poorly maintained, or a crappy bike, and you need some experience. You can buy the first two, but the third comes only with time.

I started out after not having been on a bicycle in 35 years. To offset my inexperience with bikes and maintenance, I bought a brand new LBS bike, but almost the cheapest model they had ($380, about $450 these days.)

The decent quality bike (albeit a cheap one, that was heavy as an anvil) let me focus on becoming experienced. I made tons of mistakes as a rider along the way It was also four to five months before my body was back in shape and things were flowing smoothly. I haven't missed a day since things finally got sorted out. As of the end of last week, I have 1,533 consecutive workdays of bike commuting. Given my four-day workweek, you can easily figure out that's just over seven years.

It did not go smoothly at first. The bike went on the bus a few times. And I crashed and fell off four times in the first couple of years. My first flat made me feel like a complete idiot. Maintenance I learned slowly with the help of the mechanics at my LBS, who, knowing I was using the bike as a commuter, cut the repair queue for me when I came in with questions and repairs.

Other than the odd flat tire, I haven't had to do any in-ride repairs in years. That's because I've learned how to spot trouble ahead of time, and how to maintain my bikes before trouble happens. (It helps that I also buy quality stuff.) I haven't crashed since that Pontiac hit me five years ago. Simply because variety is the spice, these days I have two bikes completely outfitted for commuting, (rear racks, full fenders, puncture-resistant tires, on-board toolkit and pump, dynamo lighting systems, backup battery lights too). But one bike can also back-up the other.

All this took time. Given time, you can turn around your record too.

+1, yes, you can get there. It was mentioned above you might need to replace a big-box-store bike with a reliable-brand bike. You can certainly buy good new bikes, but your cheapest option there is to find an older mountain bike, like $150-300 off craigslist, hopefully rigid (no suspension), buy some semi-slick commuting tires for it, if necessary pay a LBS to tune it up for you, or better, find a co-op that will teach you how to tune it up for yourself.

Other than that, while you learn, ride slower, and ride more defensively; remember it's not just cars trying to kill you, the road is also trying to destroy your bike with glass and nails and potholes etc. When you have commuted enough, you will know your route so well you will avoid every pothole, easily spot every new field of broken glass from the beer bottle that redneck threw out of his truck last night, etc.

I don't know all that much about the bike. I do know that it was built as an entry level racing bike, with a chromolly frame. I know that it was made by alpine sometime in the mid 90s, with all 105 components, and it weighs 19 pounds. Since I bought the bike for racing it looked like a good buy for my budget.

Ah, that is helpful. Your bike should be quite reliable. For commuting on rough roads, you might want to consider some beefier tires. Older chromoly frames should typically allow for fairly decent tire clearance, maybe up to 700x28? That will give you better flat resistance, and you can run them at a lower pressure which will make it easier on the rims over potholes, and easier on your body generally just on rough roads.

To avoid flats, you could also consider tire liners; I use Mr Tuffy and (for me) they have pretty much eliminated flats. There are some other brands out there as well.

I had a HUGE learning curve with tubes/tires when I first started commuting. Manhandle and tear the stem while inflating? Check. Over-inflate until *pop*? Check. Fail to check the tire for sharp objects after changing a flat? Check. Pinch the new tube in between the rim and tire? Check. Underinflate and pinch flat? Check. In time, you just learn.

Sorry to hear of all your troubles that's quite a streak of luck. I think there has been some good advice so far. But I also think you make your own luck, and bike commuting is like anything else in life. You need to do it to get better at it. With practice you'll develop your riding skills and fitness, learn about your preparation, your gear, and your systems and it will become virtually automatic and much easier with time. After 18 years of bike commuting I'm still practicing. Even though there aren't too many surprises anymore, still every day is different and i get something out of every ride. Good luck keep riding!

"a blowout just airing the tires up, twice," - Go slowly, not pinching the tube.
"rear derailleur" - Old bike? This is why i didn't buy used. Have it inspected by a shop before riding.
"hit some uneven pavement going 15mph " - Lighting/vigilance/practice and using your legs/arms to ride (looks like you needed The Art of Cycling before getting started)

Have a route that avoids heavy traffic and bad roads.

With that many flats, and then a blowout just airing it up, I suspect one of three things is happening. Either you have a small wire or thorn stuck in the tire, you need better rim tape, or you're pinching the tube under the tire. For the first, rub a soft cloth around the inside of the tire and see if it catches anywhere. If you're pinching the tube, try putting the tire on without levers, then after partially airing it up check around the rim looking at the bead, if it's not straight or it's pushed out then the tube could be trapped underneath it and it will blow with too much pressure or shortly after you start riding it. Deflate and push the tire in to set the bead better if necessary then inflate again.

it just seems to be one thing after another. I thought I finally had my tire situation figured out, upgrading my pos walmart pump with an airtower and replacing the original 20mm tires with a new set of 23s, then I had a major mechanical failure. got that fixed, had them replace the bar tape while it was in the shop, then I gave it a full tuneup, adjusting all the cables, replaced the chain, and lubed everything that moves. my next ride out I ended up in the er from a road hazard. this is my big concern at this point what can I run through and what do I need to go around.

When in doubt, go around.

+1

And when it's really dicey, choose another route.

One of the beauties of a bike is that it's far easier to go around, and it's not so punitive to choose another route. If you're not employing the flexibility of a bike, you're missing a major part of the benefits.