Both run VERY similar and make good power, The Holley SD is just a lot shorter.

The factory style hemi/6pack oil pan is more than up to the task for this combo. No worries about a deep sump hanging down on the street either.

I finally got to checking the stock replacement 3/8 NPT Melling oil pickup(two of them) to oil pan bottom clearances on the 6 quart 1970/71 Hemi and 440 six pack oil pan, the Mellings part # 63-S4 works great, the other one doesn't
Mellings only list two now for the Mopar B and RB now. The other one,63-S3, is for the deeper C body oil pans is my thinking

another good option for efi is the Fitech. For you I would recommend the 32001 600 HP kit. This is a satin finish unit and a command center that uses you stock mechanical fuel pump to feed fuel to the command center that is a high pressure pump for the efi. no need to change tanks. I have sold this to some of my customers and very good results. I think the rest of your items listed have been fairly well covered.