In theory you want the dipoles to be perpendicular to each other, to minimize interactions. That said, assuming they are going to be relatively (in terms of wavelength) close to each other and the ground, you'll probably get some coupling effects no matter what you do.
I have lots of dipoles (and other HF antennas) and some of them are relatively close to each other. I don't notice any ill effects (although maybe I don't know that I have any ill effects since I have not done before and after comparison tests, but I am generally happy with how they work).
I run all my feedlines into the shack, so I can switch between various antennas and radios. See my various posts here on the HFU for how I do this, with buried conduit and grounding blocks to run the coax, and a patch board for selecting what goes where. Coax loss at HF is incredibly low, so I am not worried about a few more feet of length. If you have only one receiver, then it might indeed be easier to only have one coax line enter the house.