I have been collecting bits and pieces to develop a prototype of this for quite a while. I purchased a Raspberry Pi 3 B+ a while ago. I had a 19" flat screen TV and a trackball and full size keyboard. I downloaded the jessie version of Raspian. This all worked fine. I had been looking for an I2S sound hat but was unwilling to pay the price. I found an imported one for half the price and got it recently. Also I replaced the TV with a yard-sale Dell monitor. To use it I got an Amazon Basics HDMI to VGA converter. It worked right out of the box! This frees up the TV for OTA antenna testing. Now, I was really struggling to get the PiFi DAC+ v2.0 working. Most of the tutorials were associated with network streaming platforms and I just wanted to use VLC locally with a handful of playlists and my music on a local harddisk. I finally created a new system TF card with NOOBS on it and I installed the latest version of Raspian and followed the instructions provided to install the sound hat on the official Raspberry Pi site. It worked! Don't know why. Seems like I did same steps.
It has been quite a while since I was able to listen to the music I enjoy.
I also added a subwoofer and plate amp to complement the Dayton B652's I had. They sound good to me and their low end goes to 70Hz but the sub takes the low end down to 40-50Hz and I have rolled off the low end of the Dayton's to about 150Hz so they don't have to put out so much sound. This is mostly a journal of what I've been piddling with. If it is helpful to anyone else, all the better.