Jay -
I've got a TC 33D (similar to your 29DA, but with a few more HP), with loaded R4 tires & FEL. I use a Woods 6 ft Box Blade. It works out fine for my needs here in the Champlain Valley in Vermont (rocks and clay is what this area is known for). I wanted the 6 footer to have enough to cover my tracks. 5 Ft is not wide enough (63" track width with the R4 tires). When I was shopping, I was not aware of any 66" options for box blades.
When working on my gravel driveway, 6 ft is great... no problems, except when going uphill on one short steep section with a full box... even then I can do OK if I drop into low range.
When working off the road, I'm OK if I'm careful about not taking too big a bite. If I bog down, I just end up making a couple of lighter passes, rather than one deep one. There are times when I wish I had more HP &/or more traction to pull it, but I'm happy with how it's worked out... especially since the percentage of time it's used on the gravel road vs off has gone up as I've finished up my off-road projects (the gravel road maintenance is never-ending).
It sounds as though we have similar soil conditions. I'd consider a 66" box blade a good match for your tractor, if you can find one of good construction. Yes, there will definitely be times when you can bog it down, but I wouldn't want to go smaller and not be able to cover my tracks.
BTW... I thought the 5 HP/foot rule was PTO HP needed for brush hogs. I've not heard it used for Box Blades... IMO, there is just too much variation in soils, slopes and type of work to be done for this rule to hold up with box blades.
Hope this helps.
John Mc