New computer build: DisplayPort not working for 2nd monitor.

I put together a new computer build with an RTX 2070S (1 HDMI and 3 DisplayPort).

Both of my monitors are VGA/DVI-D/USB/USB A/USB B from my last computer. Couple of older Dell 2009W's.

Hooking up the DVI-D to HDMI works fine on both computers.

But the only adapter for DisplayPort I have handy is DP to **FEMALE DVI-I**. And so with the adapters and cables I already have, the daisy chain looks like:

Monitor DVI-D : DVI-D to HDMI : HDMI cable : HDMI to DVI-D : DVI-I to DP

lol

Plugged in, this does not work and the computer doesn't even recognize it as a connected device on the device manager.

HOWEVER, I also have a VGA to DVI-I connector... soooooo I tried this chain:

Monitor VGA : VGA to DVI-I : DVI-I to DP.

The monitor was recognized by the computer as an attached device, it could be detected and I could set up dual screens, but nothing I could do would make it actually give a picture, it stayed out of power-saving mode.

While I'm sure getting the right cables with as few adapters as that would help, I'd also like to figure out why it's happening like that.

I've also heard about VESA needing to certify cables, are those certified cables available in DVI-D to DP for not-insane amounts of money?