I started out single-stage because I wasn't confident of my ability to handle a progressive press as a start and, loading only one rifle calibre for about a thirty-round-a-week habit, didn't really need anything more. Had I my time all over again, I would do the same (I got an RCBS Partner Press starter kit). I intend to stay with it for the foreseeable future.
If I end up reloading for a second bottleneck calibre, I will consider getting a four-hole press so that both calibres can stay set up, but it will be manually indexing.
If I give in to the desire to buy a .410/.45LC single shot rifle, just for the fun of it, I will probably get some sort of three or four hole turret press to avoid frequent die changes. (What to do about the .410 will be a separate issue.)