How has your training changed over this time?Here's more than you wanted to know:Starting running 1/1/2005
Oct 2005 - 4:49, trng Bob Glover 18 week 20 mpw base/peak 40 mpw
Mar 2006 - 4:16, trng Pfitz 12/<55mpw
May 2006 - 4:00:03, just easy running between, getting to ~60 mpw IIRC
Oct 2006 - 3:56, trng lots of consecutive 55-60 mile weeks of easy running
Nov 2006 - 3:43, more easy 55-60 mile weeks in between
May 2007 - 3:24, more easy 60mpws with frequent races over the winter and then 12 weeks of Benji Durden's plan - ~55mpw but with tempo and intervals
Oct 2007 - 3:27 (3:15 pace through 18 and then died), trng was Pfitz 12/70mpw scaled to about 67 peak
May 2008 - 3:21, many 70 mile weeks, cut back to ~50 ever 4th week, peaked at 80. 2 med long runs and 1 long run per week. 1 of the MLRs might have 5 at MP or intervals or tempo
Basically, I've just increased either mileage/intensity over time.
And I have to ask what motivated you to do some of your marathons nearly back-to-back rather than getting a decent recovery before the next attempt?
You phrased that as tactfully as you could I guess

What motivated me was not wanting to have to think about it for six months. The 4:16 was on a freakishly hot, sunny day and I had been working to break 4:00. The 3:56 was just strange. I had run much more than I ever had and run a 1:40 half as a tune-up, so I was disappointed in 3:56. I doubled down 4 weeks later and ran 3:43 and didn't have to think about it over the winter. I'd seen so many people doing a marathon every week on coolrunning that 4 weeks didn't seem so crazy (I used to be active on coolrunning before active took over). It's not really that big a deal if you're doing enough mileage. Don't try to do to much in between those marathons though!
Do you think you underestimated your abilities the first couple years
No, I was running as fast as I could!
or do you feel that you trained equally well each time out but just took some years under your belt to improve your times and fitness to this level?
I've trained more (intensity and/or mileage) each time, but I think the premise of the second part of your question is correct. Consistent training over time is needed for long term improvement and it can take a while before you realize the gains. Your time is a result of what you've done in the months and years before the race, not just in the 16 week training schedule.