Need advice on how to dip a toe into digital

The simplest system I can think of is iTunes (free) and an AirPort Express ($99) for streaming and D/A. I use iTunes, on an iMac, and an AirPort Express for streaming and Toslink cable from the AirPort Express into a Pioneer Elite receiver to perform the D/A conversion. The results are very good to my ears.

The other option is to pick up a cheap Dac and connect the laptop directly via USB. The Schiit Modi Dac is only $99 and comes with a 15 day money back guarantee.

Thanks. Is SACD something to think about?

I think the easiest way to dip a toe it to get a free player (jriver - free, itunes if a mac, or foobar) and get a audioquest dragonfly outboard dac. output this to a amp, receiver or what do you have? and try it out. I'd skip worrying about sacd or dsd or many other acronyms and see if you like it. I would take some care in ripping your cd's to your laptop. a couple minutes ahead of time may pay dividends later if you continue. several free programs like Exact Audio Copy will work just fine for you. If your a MAC guy consider ALAC and if a windows guy maybe FLAC. both are compressed but also lossless. Avoid mp3. very lossy. you can always go there later if you dont care but you cant go from mp3 to lossless unless you like fooling yourself! total cost about $250. option that may (depending on your system) would be other dacs like the HRT or peachtree idac. too many others to list here. just have fun.

Two questions ... what is your budget for dipping a toe, and what is motivating you to do so (or to put it another way, is it just a matter or curiosity or is there some particular problem that you are hoping to solve)?