That block is why I say either build a common easy to find and cheap 390 block and make a 445 out of it or buy an aftermarket block like a BBM or Pond. Just saw a .017" over S/O block sell for $3,200.
As to blocks cracking, it is not just FE's that crack at the main oil feed hole up to the cam, are a lot of other cam in block blocks do the same. Other place common is at the main cap bolt hole. Best advice be use a light rotating assembly, balance everything, and keep the engine out of Detonation! Fun fact on at least the early 427 blocks Ford machined the main oil holes at the mains wider so guess they were more concerned with oil to the crank at the time. I would not recommend do it today as not needed.
Regarding the reason for the side oiler, only reason Ford did it was for NASCAR use where had to go 500 miles at 7,000 rpm. They also widened the rod journal and had special bearing made. This was to increase the load bearing area. The other thing they did was cross drill the crank which cause oil starvation at high RPM. The solution enough oil pressure and more direct feed path (Side oiling) to over come the centrifugal force making the oil go the wrong direction in the crank. Also keep in mind NASCAR made them sell this stuff in cars back then to be legal to race.
As said the T/O oiling system is similar to a SBC and nobody complains about SBC oiling. The difference is the SBC does not oil the rockers off of #2 & 4 cam bores and the rod bearing is wider. The FE has one of the narrowest rod bearing of any American V-8. Want to improve the oiling on a T/O FE? other than a good pan would be oil the rockers via lifters and block the rocker feeds. Find some cam bearing that are not drilled and drill the cam feed holes smaller to restrict the oil to the cam and use a cam that is not grooved at #2 and 4 journal. Finally use a crank with a BBC rod jounal sizing. Of course good luck finding a non-drilled cam bearing, but anyways that is my 2 cents on the subject.