That is a strange problem. I use a 530 with Windows 8.1, with a Z87 board (not yours). I switch between two Dell monitors, a U2312HM and a P2714, using DisplayPort and DVI cables. I am using the Intel 4600 graphics on my i5-4670K. I've never had the issue that you have, the PC boots fine every time.
I have had some slight detection issues, such as a BIOS utility that shows components connected to the board, not seeing the 530. It never fails to boot given that. The new DC32 firmware fixed the slight detection issues.
Are you using the Intel IRST driver? I'm sure it is available on your board's download page. Or are you using the standard Windows 8 storahci SATA driver?
I use IRST 12.8, which has several power and performance options that can be configured with the IRST Windows software. Those are unique to the Z87 chipset. If you use IRST now, you might want to check those settings. I can enable DIPM, and set DSA (Dynamic Storage Accelerator) to the lowest setting, with all C-States enabled including C7, and my 530 works fine.
I know Gigabyte has a "hotfix" for at least some of their Z87 boards, that is used with the IRST driver, to fix drive detection issues. They've had quite a few user issues with drive detection, of any make of SSD or HDD.
I'm curious regarding how a digital monitor interface like DP can be sending "power feedback" to the video source, which then affects other components.