I don't like having to install or remove something in some strange sequence. That to me is a poor design..
I don't know if the headers you have are bad or not... But when working in a very limited area, you have to design everything just right- the OEMs have done this for years- usually in favor of quicker assembly and not in favor of maintenance.
On both of my current rigs, the header challenged me. One set was the Hedman long tubes on a 302 block (347)- wiggling them into the engine bay sucked. Then getting bolts started had to be done in such a way as to get the flange close for some after getting the bolt thru the hole. Then I either had to have a special wrench to tighten some of them or use socket head cap bolts and an allen head socket.
On my BC broncos shorties on my 351, the issue was again with installing the bolts and was similar to the long tubes- they were ceramic coated and easier to locate without scratching. These I did with no body forward of the firewall (crawler build).
Neither are a bad design and both are designed with proper flow dynamics over ease of install. Heck the BCB shorties have a much bigger primary tube, making it even harder! Patience was the key and I have very little of it.
One last note- with the leak at the back two tubes, I wonder if the back of the header was loose and it rested against the trans...