Howie, I'd planned to try precisely that. Set the pushrods down through the heads and set the entire rocker box/rocker arm assembly down over the top. If it'll work without taking the extra bits apart down low that's great. Just don't know yet if it will.
Front hole will obviously allow plenty of room. Don't know if back hole will though. One of those "just have to try it and find out" kind of things. If not popping off a lifter block is no big deal for an extra.
Maybe I'm missing something here, but it seems this is making it harder than it is! The TP rocker boxes allow the rockers to come out easy. What I do is set the rocker boxes down on the heads with out the rockers. Bolt everything down, put in the tubes and drop the pushrods in. Then I put the rockers on. With the TP's, if you have to pull the pushrods, I just take out the one bolt holding the shaft and pull the shaft out, leaving all the other bolts in. There is a screw hole in the end of the TP rocker shafts that make it easy to pull it in and out.
Perhaps the problem is you did not use the TP engineering rockers and the shafts supplied did not have these screw holes?
Another big problem I see with the TP rocker box is the supplied grade 8 bolts used for the rocker shafts, they are shorter than the stock ones. You run a good risk of stripping the holes in the head with these bolts. I replaced mine with allen head bolts the same length of the stock ones. They are a good 1/2" longer than the ones TP supplies.