If it were me I'd stick with the one you have that is working simply for one reason, the longer you hold on to it, the more newer monitors will improve and get cheaper, so the longer you wait with one that is doing the job, the less you'll eventually pay for a replacement at better quality. With regard to widescreen, as far as playing older stuff goes, most widescreens have the ability to alter the aspect ratio, so you can adjust it from the letterbox shape to a more traditional shape if the image is distorted in your old software, so not a big deal on that score. The important thing to look out for on TFT monitor types is the contrast capability, compare a few and you will see that the higher the numbers, the better it looks, so weigh that up too if you are going to get one now.
Personally I am dreading the day my big CRT monitor dies, as I'll have to use a more modern one to replace it, and while it is true they are improving in color repro, currently TFTs are nowhere near as good as the big old CRTs. TFTs are awful for training people on too, for the simple reason that if you are training a room full of people all on TFT monitors, you have to walk right up behind them to see that they are using the correct things if they get in trouble with what you are talking about, because you can't see the screen display properly at oblique angles from a distance, which you could when it was CRT monitors. One walk around a TV shop that still has a few CRT TVs on display will confirm that, as will the fact that ICC colour profiling in programs such as Photoshop actually now has an advanced saturation correction option, to allow for the crappiness of TFT monitor colour display.
In complete fairness, I will say that the water in Dangerous Waters looks better on my laptop's TFT than is does on my big old CRT though, not quite sure why, but it does!
Chock