Remote work in the 90s and 00s was a lot of FTP, CVS, email and IM. Long distance phone calls still cost money for much of that time too, so there wasn't much synchronous phone calls, once a week or so. Also, generally the business needs were either high enough that the staff were all expert-ish and could get done what they needed, or low enough that random Bob's cousin's nephew could build it in HoTMetaL. There wasn't a lot of in between.
When I worked for other people, management spent a lot of time with requirements and specs before implementing, which often resulted in mismatched software expectations. Agile gets poo-poo'd now, but it was a revolution at the time
When I was doing my own consulting, I always did my best to find local clients for remote work (often building e-commerce web sites when the competition was still using FrontPage) because it was preferable to be able to call the client or meet in person to discuss the inevitable requirements snafus.
Honestly, it doesn't seem that much different now. Humans are generally not all that great at communication. The tools we have today make a dent in that problem but there's still significant unresolved challenges.
When I'm leading teams, I tend to spend a lot of time on teaching people to communicate more effectively and creating processes to enable it. It makes things go more smoothly than trying to be the central hub for all communication.