Myself, I grew up with records and cassettes. Of course, the '90's (and half of the '00's) for me were CDs CDs CDs. But going back to my dad's record collection, nothing sounded like the stuff from the '70's, and the CDs I had (of the same albums) just didn't compare to the real thing. You can still get that sound today, but it means keeping your signal chain fully analog from start to finish. Maybe it is subjective, but it still sounds better, and I'm hardly the only one that thinks so. That's why I choose to work with tape.
So yeah, I started recording digital back in school, which was my first exposure to ProTools. Of course, I didn't know how to do all that cutting and pasting and was just learning punch-ins. Even these days I'll record digital for some stuff. I'm working with a guy trying to compose music for him to use in his youtube videos, and it really helps to be able to repeat a two-second phrase over and over ad infinitum, since all he really wants are drum loops. With digital, I can knock something off and send it to him via email in just a few hours. Digital TECHNIQUES and progressing technology will always have the advantage of being more expedient.
The thing is: is this good?
I'm working on this right now as I'm reading Theodore Sturgeon, and he had the problem nailed more than 50 years ago. Sure, technology is wonderful, and can help us do amazing things, however, we're all too ready to be slaves to convenience, and it's a hard cycle to break.
It's an argument that goes way beyond the analog vs. digital debate. There's a discipline that has to be learned, true, but you'd be better off for having learned to do things "the hard way," as it were. When you learn guitar, it's much better to start off on an acoustic than an electric. If you learn to ride, you'll get a lot more learning English rather than Western...if you can ride English style, you can ride anything. This goes to damn near every facet of life. Over the last 6 months, I've been learning how to do pastry shells from scratch. Sure, I could go to Kroger and buy anything I wanted to pre-made; does that mean that there is nothing to be gained from being able to make pumpkin pies and Cornish pasties in my own damn kitchen?
I get shit all the time from people who are stuck in their ultra-modern way of living, and are too set in their ways to change. The thing is, that all their arguments seem to come back to the premise that digital is easier. Not better, but easier. Now, they usually argue that digital is better because it is easier, but really, they ultimately end up sounding like a fat kid expounding the virtues of donuts over green beans. Even when they concede that I'm right (and most do after I yell at them enough), they admit that it's not worth it to them to change their evil ways. Here's a biblical example: Matthew 19:16-26.
OK, I'm starting to get more tongue-in-cheek the longer I write, but I hope I've got my point across.
I applaud that you are at a crossroads, and are willing to make a commitment to record on tape; a lesser person wouldn't even consider it. My advice is to get the 388 and fully embrace tape. Yes, there will be a learning curve, and at first it could be hard, but you'll be a better person for learning a new discipline.