Looking back:
Hardware based:
I would have gone rack-mount WAY sooner, would have started to play with Linux sooner, would have started on gigabit hardware vs. 10/100 and "upgrading later". (gigabit just makes remote desktop and file transfers easier, no real trading impact IMHO), would have built out my BackBlaze 2 years ago... this thing is awesome. Also, learned the hard way that Hardware RAID > Software RAID. Going up to 8GB RAM per machine only helped in simulation boxes - 4GB RAM is just fine for execution boxes.
Software Based:
Learned the hard way that SOFTWARE based RAID is not hardware based RAID. W7x64 is awesome, stayed on XP & XPx64 way too long. Excel 2007 is worth every penny and is far superior to 2003. Paying for software is always a must - torrenting is not legal and WILL come back and bite you (a good friend learned the hard way). Paying for Matlab is dumb, decent programmers can use R (free, open-source) just as easily.
Trading Based:
Execution speed games are for big boys. HFT is for big boys. Leave the big-boy trades to the big boys. Arbs/Market Neutral (attempts at riskless trading) exist but go away quickly, it is very hard to build a career/steady income on trades that last 6 months to 2 years then go away.
Happy about:
Happy I had to learn/DIY hardware & networking. I now know/understand a lot about computers hardware and I'm much better off for it. Good, clean tick data is priceless, do it right, pay for it and protect it. I got lucky on the tick data front.
In my experience, partnering with other traders has been a very good thing. Trust is hard but if you can trust someone then two sets of eyes & experience is always better than one. Also, its good to diversify as much as possible - going it alone is a losing uphill battle IMHO.