I used the basic Wintersteiger iron for a couple of years, and I was pretty happy with it, until I started using some higher melting point waxes. I also started to crayon the wax, and iron through a fiberlene paper. At that time, I found that the temperature fluctuations on the Wintersteiger are too wide. Basically, I had to either crank it up high enough to work all the way through, but it was getting close to the point of messing up the P-Tex, or having to stop every couple of feet to reheat, because the iron would "freeze" to the ski.
So, since I'm a gear whore, I splurged on the digital Toko, and there's just no going back for me.
First, the temperature range is much tighter (probably less than 10 F), vs something like 20 F for the Wintersteiger.
Second, using the crayon+fiberlene method, I'm saving a huge amount of wax. I'm easily using a 1/4 of the wax I used with the drip method, and that's a pretty accurate statement, not a WAG. In the first year, I've saved about $30 to $40 on the wax. I've used 250G of base wax the year before, and about 50G with the Toko. Similar ratio caries over to the wax-of-the-day.
Third, the reduction in the amount of wax used, allowed me to start playing with some fluoro waxes which would be far too expensive with the drip method.
Is it truly cost effective? Probably not, but it really is a joy to use. I wouldn't hesitate to replace it, if I had to. If it lasts 10 years or so, the cost becomes negligible.
Anyway, not saying that a $100+ iron is a necessity, it's a luxury, but we're in an expensive sport, and it's all about rationalizing the cost for yourself.