You can calculate the feedline losses using VK1OD's handy calculator:
http://vk1od.net/calc/tl/tllc.phpWith 100m of RG-213 on 40m the loss is 1.7dB, and 2/3 of your power
reaches the antenna (assuming a low SWR.) Losses are lower on the
lower frequencies: on Top Band the loss is less than 1dB. That's
probably good enough, but there are other sorts of coax with even
lower loss. (I have a suitable piece of RG-17 out in the barn if you
want to come over and get it, but it takes two men to move it.)
I've used large horizontal loops of various types, with generally good
results. But as Mark says, you have to look at the radiation patterns
and see how they meet your needs. A full wave 80m loop fed in
one corner, for example, tends to radiate off the corners on 40m, 20m
and 15m, with nulls off the sides. On 10m it has 8 relatively narrow
lobes. it also depends how high you can install it, and the expense of
4 support masts (unless you can hang it by ropes from the surrounding
buildings.)
By contrast, an inverted vee only requires one tall support, or 2 or 3 for
a dipole/doublet.
The radiation pattern on 160m will be about the same for all options, but
on higher bands there will be a lot of variation, with various lobes and
nulls. (This also applies in the vertical pattern, so some idea of the
distances you want to cover and the required radiation angles to do so
will also come in handy.)
Multiple dipoles (cut for each band) on a common feedpoint, or a trap
antenna, is probably best if you are using an inverted vee, as it keeps
maximum radiation from the highest point in the antenna. Multiband
performance drops off as the slope of the wire increases.
Another option to consider is relay switching at the base to change the
antenna arrangement. For example, if you use an 80m doublet fed with
a quarter wave of parallel conductor line down to ground level, you can
feed it in normal doublet mode on 80m and higher (it might not work as
well on 160m due to the short length), or connect both feedline wires
in parallel and feed it as a vertical against ground, which would be
effective on 80m and 160m (and likely on 40m as well.)