Linux driver support was hell from roughly around 2010 to 2016. Both major GPU manufacturers had awful proprietary drivers (with even worse packaging), and most wifi chipsets required proprietary firmware blobs to work at all: which was very tricky to package, because of copyright bullshit.
This was also the era of major desktop environments playing fast and loose with there UX. GNOME3 was released in 2011. Ubuntu started defaulting to Unity in 2010, and started their Wayland competitor (Mir) in 2014. KDE Plasma 5 (2014) defaulted to fancy composting, and felt really bloated relative to the others. The only desktop environments that really kept true to the good old days (~2008) are XFCE4 and MATE (the GNOME2 fork). KDE5 isn't bad, either, but it's still a bit too bloated.
The other problem caused by proprietary video drivers was package versioning. It's tricky to have the right kernel version and Xorg version necessary to run a proprietary video driver blob; and keep the rest of your system up-to-date. Ubuntu found its initial success by creating a generally stable package repository roughly as up-to-date as Debian unstable. Unfortunately, Ubuntu became a bloated mess with strange things like Unity and Mir bundled in. Archlinux has been a good alternative, but it does expect a level of familiarity with shell utilities. Linux Mint (an Ubuntu or Debian fork) is still my first recommendation to casual users. One of these days, it will be NixOS, which is a giant leap in stability and package versioning.
The last change of that era that has been breaking the Linux experience is the switch from BIOS/MBR to UEFI/GPT. This shift was slow and messy, with most hardware adoption following the release of Windows 8 in 2012. GRUB used to break in one predictable way: windows overwrites the MBR, replacing GRUB with its bootloader. Now, with UEFI, boot entries are saved directly to the motherboard, and the bootloader itself lives in the ESP partition. The windows installer will put its bootloader in the first ESP it can find, and you don't get to choose which one that is. Now you have to worry about the ESP running out of space, but that's about it: everything else has been generally resolved, and the UEFI bootloader experience is very solid (apart from the windows installer caveat).
Now that AMDGPU is mature, and NVIDIA's drivers are relatively well maintained (and packaged), the Linux desktop experience is even more stable than its heyday back in 2008. If you install a distro that targets relatively recent package versions, like Archlinux, Linux Mint, or even Fedora; and you use a solid familiar desktop environment like MATE or XFCE4; you can avoid most UI/UX clunkiness and have very little need to fiddle with your package manager. Boot issues are pretty unlikely now, so long as you install in UEFI mode (not legacy BIOS emulation), and completely avoid MBR.
This was also the era of major desktop environments playing fast and loose with there UX. GNOME3 was released in 2011. Ubuntu started defaulting to Unity in 2010, and started their Wayland competitor (Mir) in 2014. KDE Plasma 5 (2014) defaulted to fancy composting, and felt really bloated relative to the others. The only desktop environments that really kept true to the good old days (~2008) are XFCE4 and MATE (the GNOME2 fork). KDE5 isn't bad, either, but it's still a bit too bloated.
The other problem caused by proprietary video drivers was package versioning. It's tricky to have the right kernel version and Xorg version necessary to run a proprietary video driver blob; and keep the rest of your system up-to-date. Ubuntu found its initial success by creating a generally stable package repository roughly as up-to-date as Debian unstable. Unfortunately, Ubuntu became a bloated mess with strange things like Unity and Mir bundled in. Archlinux has been a good alternative, but it does expect a level of familiarity with shell utilities. Linux Mint (an Ubuntu or Debian fork) is still my first recommendation to casual users. One of these days, it will be NixOS, which is a giant leap in stability and package versioning.
The last change of that era that has been breaking the Linux experience is the switch from BIOS/MBR to UEFI/GPT. This shift was slow and messy, with most hardware adoption following the release of Windows 8 in 2012. GRUB used to break in one predictable way: windows overwrites the MBR, replacing GRUB with its bootloader. Now, with UEFI, boot entries are saved directly to the motherboard, and the bootloader itself lives in the ESP partition. The windows installer will put its bootloader in the first ESP it can find, and you don't get to choose which one that is. Now you have to worry about the ESP running out of space, but that's about it: everything else has been generally resolved, and the UEFI bootloader experience is very solid (apart from the windows installer caveat).
Now that AMDGPU is mature, and NVIDIA's drivers are relatively well maintained (and packaged), the Linux desktop experience is even more stable than its heyday back in 2008. If you install a distro that targets relatively recent package versions, like Archlinux, Linux Mint, or even Fedora; and you use a solid familiar desktop environment like MATE or XFCE4; you can avoid most UI/UX clunkiness and have very little need to fiddle with your package manager. Boot issues are pretty unlikely now, so long as you install in UEFI mode (not legacy BIOS emulation), and completely avoid MBR.