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Good point, although most of my collection are new releases/reissues which I'd expect to have well mastered digital release.
I thought generally there's more risk of a record being cut from a CD master rather than a poor digital master accompanying an analogue master on record.
neu-
It might be best to concentrate on buying releases that have some ambition to be good on vinyl.
e.g. Surprise Chef - All News Is Good News on Mr Bongo
Analog recording of a band playing live with a label that doesn't charge the earth but believes in vinyl.
There are no hard and fast rules and personal preference is going to dictate the pool of releases that you can choose from but it's a lot of kissing frogs and some times a prince comes along.
Airhead
Audacity will do the job. I use Logic Pro because I already had it and know how to use it easily. I also catalogue everything using Discogs because I sell on there and I can use the Discogs release code to create tags for the digital files using Yate.
I wanted the sound of vinyl as a digital recording ?!? It does depend on what you are buying as to whether analog masters would even exist. It seems like the 'loudness war' has abated a bit in some areas of music but generally pop is mastered with quite a bit of compression because psychoacoustically louder is better, it also stands out in the playlists or transmissions by being louder. It's harder to do that when mastering for vinyl although it's still possible to produce a highly compressed pressing on vinyl.
I also enjoy the physical nature of searching through a vinyl collection although it is a pain in the ass to have to handle so many records all the time.
If you're not addicted to vinyl yet then save yourself before it's too late!