To throw my 2c into the pot, I know where you are coming from. Just like you, I never buy the latest or the greatest out there.
Last year I upgraded my graphics card for a nVidia 1060 Gamers Edition. The reason I went for the "Gamers Edition" is because it has 6Gb of RAM instead of the standard 4Gb. Extra RAM in any graphics card is always welcome! The graphics card has three outputs: 2 x HDMI and 1 x DVI. No VGA anymore! If I had to do the same upgrade now, I will probably go for the 1660, which is slightly better.
I have recently plugged a second monitor onto my system and the graphics card runs both equally well. My main monitor runs on HDMI and the second older monitor on DVI. Having a second monitor is a real plus when it comes to work. You can open files on both monitors and easily copy and paste between the screens.
If your monitor does not support HDMI or DVI, there are plenty of converters around that will allow you to connect any older monitor to any newer graphics card.
Hope this helps you.