Yeah it was pretty rough up until the late 2000s. I had been running iMacs so video output add-in cards weren't an option so I had to resort to a variety of different tricks to achieve the desired result. One of the last ones I remember trying involved some sort of hijinks with my TiVo box to get it to pull stuff from my computer.

I eventually just gave up and watched things on my iMac G5 since its 20" screen wasn't all that much smaller than my CRT TV, and then later in college I upgraded to a 27" Intel iMac which had a nice IPS panel display and was better to watch things on than most flat panel TVs from that era around that size.