Here's a bit of irony for you:

I want to get a Trek Portland next year if I'm still bike commuting. Worthwhile investment.

I also want to get a cheap low-end bike and a decent U-lock for high-risk commuting, like going down to Baltimore's inner harbor at night and leaving the bike shackled up outside on the street for several hours. (Parents have expressed that I'll get shot or knifed on the way home, depending on the race of whatever people I meet along the way; I generally ignore this advice)

Now, for my expensive bike, it makes sense to buy something like a $150 set of Pitlocks with front and rear wheel, headset, saddle, and brake locks. Too bad there's not a lock for the derailleur or brifters but eh.

... except that's not the bike I park in high-risk conditions.

So, the inexpensive bike would ... get ... a hardware upgrade that cost me more than the bike itself.

Do you see it?

I guess I don't see the question here. If you are concerned about paying the money, weigh the pros and cons. If you really think losing components is going to be a problem, you may need to drop for the locking system. Personally, I like to use two u locks, one for each wheel attached to a fixed point. Never had any problems. Get a locking system for your saddle, and you should be good to go.

Folklore has it that bike messengers say you should spend more on your lock than on your bike.

In a high-crime area, you can sort of see the logic. Doesn't make sense if your bike will only get stolen once, but if it's going to get stolen repeatedly, the lock more than pays for itself.

Get the Pitlocks, so I can enjoy them vicariously :-0

Depends. Figure miles travelled per dollar invested in bike vs car mileage etc. you still come out ahead. I leave my locks at work site attached to rack there. Ride in lock up.... Have been fortunate I will admit no one has messed with my bike components. Have heard urban legends of bad things done to bikes but have not seen this at my location specifically. YMMV.

I have Pitlocks on three of my four bikes. Two of them are my highest value bikes, and the other is my lowest value bike. It's not so much value that drives my decision, but rather that I'd like to have everything still there when I come back to the bike. It's less of a pain in the @$$. Besides, I'd look silly riding the bus in full kit and a helmet.

The fourth bike doesn't get used for errands or commuting, so it doesn't need Pitlocks. Even so, it has bolt-ons instead of quick-releases.

Hmm. I'll talk to my local bike shop about stocking Pitlocks, too. Locking up the wheels with a cable lock is silly; lock the whole bike with the cable and forget the U lock, why don't ya? Not to mention saddle and seat posts ... of course, no way to secure a saddle. Mine can be removed by hand + allen wrench (two bolts, one is hand-tight).

I've tried Pinhead skewers/pitlocks to secure my wheels and seat post collar but find the cost shipping from Pinhead to be extremely prohibitive to getting a complete matched set for all my bikes. As a result I've mixed and matched the Pinhead locks with the more expensive components, applied less expensive secure skewers and such amongst the bikes and anything else gets a complementary cable run through to my U-lock.

One last thing I do to make my bikes less desirable to thieves: quick release pedals. A bike with no pedals to pedal is sure to discourage the casual thief. Probably not so much the professional thief with a pick-up or van full of tools and stolen bikes. I hate that guy. He's such an a$$hole.

Along that line of thinking, you can just tie your bike up with a string why bother with a cable lock?

You use the ulock because it's far more secure than the cable lock alone.

What are you implying with this statement?

What are you implying with your implication?

Someone will just cut the cable anyway and steal your wheels, and then you have to walk 10 miles to get home and spend $200 on wheels + cassette.

When I moved out, my parents said I wouldn't survive on my own because there were too many black people and I'd get shot and robbed and whatever. Once I walked to a bar at night and they told me I'd get gutted by mexicans.

Once in a while, my parents call me crying because I never talk to them.

If you're not adverse to carrying 15lbs extra, get a heavy chain and a U-lock combo. This provides as much security for your wheels as Pitlocks + a Ulock, and will cost you about $80 for both, instead of the $150 that you quoted.

It will also give you more versatility because the chain is able to lock around objects that a Ulock does not fit around. The downside is weight, but that should be 'ok' if you are mostly riding in flat terrain.

Heh yeah, the break for a pitlock is a handheld dremel rotary tool with a cutter wheel, slice a flathead slot in it and use a big flathead attached to a break bar (these are easy to get). The break for a chain is a dremel too, or bolt cutters and another chain if you don't mangle the bolt cutters trying to chomp an ultra-hardened chain.

Uh...ok.

I have a set of Pitlocks and use ball bearings stuffed in all the most vital screws through out my LHT. This set up has served me well so far, as I occasionally have to leave it locked up(NY U Lock) in Belltown for 6-10hrs. Each time I arrive to my bike fully intact.
If a thief were to use a portable grinder to get the wheels off, why stop there, might as well focus on the U lock and get the whole thing.

... Touché

Thanks for explanation bluefoxicy . It sounds more like their problem than yours.