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Converting half barrels into planters

in Fruit & veg
Hello! We have acquired two half-barrels and would really like to convert them into planters, probably to grow beans/peas up some wigwams. At the moment the barrels have no holes, however are old enough that they are not completely watertight either.
Questions:
1) If we want to plant straight into the barrels, is it best to drill holes in the BOTTOM or the SIDES? Our thinking being that the bottom would allow better drainage, but maybe the side (like 10cm up maybe) would allow better water retention in the base, to allow the plants to cope better when watering isn't so frequent.
2) Is it worth the hassle of making them into self-watering/subirrigation style planters? We think we'd have to line them first to make them waterproof for the reservoir, but it would be possible, just not sure it's worth the effort.
Thanks all!
Questions:
1) If we want to plant straight into the barrels, is it best to drill holes in the BOTTOM or the SIDES? Our thinking being that the bottom would allow better drainage, but maybe the side (like 10cm up maybe) would allow better water retention in the base, to allow the plants to cope better when watering isn't so frequent.
2) Is it worth the hassle of making them into self-watering/subirrigation style planters? We think we'd have to line them first to make them waterproof for the reservoir, but it would be possible, just not sure it's worth the effort.
Thanks all!

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