Here is the process I have evolved to over the years. My main music player for many many years has been Windoze Media Player, simply because it always seemed the most intuitive and easiest to use when organizing my music library. I have looked at other players over the years, and found all of the ones I tried to be lacking SOOooo much of what was important to me, so I just quit looking at anything else except WMP. But now the idiots at M$ have started jacking around with WMP under Windoze10 - does not even run on some computers anymore! So I just found MusicBee in the past few days, and I think I am going to like it.
Now to the real subject of your post - what format to use. I have made some dumb decisions over the years, and I have evolved there too. I used to be bit of a real audiophile - huge expensive systems back in the 70s before modern electronics wiped out so many of the quality differences. When I started moving all my music to the computers for ease of access and organization, I insisted on going totally lossless, but I always struggled with the extra large files and lack of available players for my preferred formats. I hated all things MP3 (for mostly irrational reasons), and I eventually decided to just stick with WMA lossless since I was married to WMP. In hindsight, it was not a very good decision. Now that I am getting old, I do not listen to music the same way I used to, so I have revised my entire plan.
First of all, I finally decided that I just had to let the evil M$ empire go and get totally away for as much of their proprietary BS as possible (the same way I have felt about Apple for 30 years). And when I reconsidered how and when I listened to music these days, I decided that only rarely did the full lossless quality make any real difference. Furthermore, as long as I had the original CDs in my possession, I could always access the full lossless format if I wanted it. Vinyl album rips are a different story, both in ease of access and available quality, but I'll leave that for another time.
So here is my current process: Where I have the original CD, I keep either a medium or high quality MP3 rip in my library (depending on the type of music and inherent complexity of detail). If I no longer have the original CD, I seek out and keep a FLAC copy if possible, or at worst a highest quality MP3.
It is taking me a very long time to slowly work through all my old WMA format files to replace them, but even that is getting easier with MusicBee's ability to convert all the formats without having to re-rip them.