I have made several PCBs at home and I've been making them for a long time. Everytime I make one, it is better than the one before, because I find ways to optimize the processes involved: what is the best paper for toner transfer, the adequate temperature and time for the transfer, and so on. I like doing them and I enjoy doing them.
All my boards are single-sided, and I take care in revising the routing made by DipTrace (more on that later). I don't trust its auto-router blindly. A good PCB starts in the PCB layout: I know of the limitations of my process and I take care in specifying trace widths and clearance I can handle (18mil). I avoid jumpers. I revise DipTraces autoroutes and end up changing or correcting at least 50% of them.
For drilling the boards I use a Dremel tool exactly like this: http://toolmonger.com/wp-content/uploads/2007/04/post-dremelworkstation.jpg
I have drill bits in 0.6, 0.8, 1.0 and 1.2mm.
I know my homemade PCBs could look a lot better if I were using photographic transfer methods, a better etching process and so on, but I like to keep it simple and cheap, so I use toner transfer with glossy magazine paper, transfered with a cloth iron and etched with (warm and filtered) ferric chloride. This is very cheap and very fast. For me, designing the board as well as I can is what gives me high sucess rates.
Here are a couple examples of PCBs I've made. Both are links to Facebook albums, but no facebook account is required:
1) Simduino (Simplified Arduino clone): https://www.facebook.com/media/set/?set=a.3248657275029.110252.1824874327&type=1&l=f89646a4f1
2) Arduino shield (with EEPROM + RTC + dig. temp. sensor): https://www.facebook.com/media/set/?set=a.3191611048909.108905.1824874327&type=1&l=a0e77a5b55
About DipTrace: I like it very much. I does everything I need (my needs are pretty basic and simple). Now that I've learned how to create custom components and patterns on it, there is very little I can't do with it.
Only TODAY I sent my first order to iTeadStudio, because the PCBs had to be double-sided and I needed10 of them.
In short, I find designing and making PCBs a great fun and I really enjoy making them.