I don't know how well it would work out in the long run, but it's something that'd be interesting, at least at the start.
While Jim Ross will always be known as, in my opinion, the best commentator in the business; I do think he could be a strong manager as well. Jim Ross is someone that has near limitless passion for wrestling and always has, so giving him a small stable of guys to help get over MIGHT be something that MIGHT work. Personally, I think if Vince allowed Triple H to ultimately have say over such an angle, it has a much better chance of succeeding. Like JR, Triple H has much more of an "old school" mentality when it comes to certain aspects of the wrestling business and I think they could come up with something that has potential.
I think a big part of it, however, would be who Jim Ross' boys are. It's tempting to go with guys who are already on the roster but, personally, I'd go with new talent from NXT with maybe one or two guys on the main roster like Barrett and/or Cesaro. Fresh talent to go with a fresh manager as part of a fresh angle. Jim Ross is quite probably the most beloved non-wrestler in WWE since Bobby Heenan & Gorilla Monsoon, so I don't think fans would have a problem rallying around him. At the same time though, the wrestlers paired with him would need to be able to carry their own weight.