Kegging is easier, IME. You have less things to sanitize, carry around, etc. I've even gotten to the point where I push from fermenter to serving kegs with CO2. I can keg 6 gallons in maybe 10 minutes that way. I also don't need to lift the fermenter from where it's been sitting in order to keg. With proper sanitation practices (or normal ones), you have far less risk too.
For carbonating stouts, you'll still want to use CO2 for that. The nitrogen, or beer gas, setup to use a stout tap means you'll want to carbonate on CO2 first. Then transfer to beer gas for serving. Depending on how you set the beer gas regulator, you can have loss of carbonation in the batch over the time it's on tap. IMO/IME, you can do very well with a Perlick 575 'creamer' faucet and the correct CO2 pressure set (see the chart
here). You won't get the cascade effect in the glass, but you'll still get a great beer into the glass.
As far as bottling goes, I still do some of batches. BUT, I bottle from keg now (once it's fully carbonated). This way I have much tighter control over the carbonation level and don't need to worry about it being either too high, or too low, for the brew. Plus, I can bottle a few to take with me when I wish and don't have all those bottles to store. Granted, I still have plenty of bottles from when I was bottling beer. I'm seriously thinking about either selling most of those, or giving them away to other area home brewers. I'll keep some of them, of course, but I can get rid of a good amount too.
