Self sufficient on Mars? It's got such a wispy atmosphere the only real benefit of Mars vs orbital which you get is gravity without needing to spin something. Dropping a tube of air with a sulfuric acid resistant coating into the upper Venusian clouds really isn't harder than making something which has to sustain slightly less of a pressure differential than an actual space station. You punch a hole in your Venus cloudtube and it stinks, you punch a hole in your Mars dustcanister and you're going to experience what might be a very interesting death.
You fall to get to Venus, you climb to get to Mars, I mean, yeah, watching boots on soil would be a neat stunt while elsewhere dudes are living in a literal cloud city and discovering how long it takes to get sick of "I have altered the deal" jokes.
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It's actually HARDER to "fall" in the Solar System than it is to go out. Weird consequence of orbital mechanics. In order to "fall" (highly inaccurate verbiage) to Venus, you have to slow your "sideways" motion. Perhaps it's easier to explain and think of in an energy sense:
Things in larger orbits ("higher" orbits, perhaps) have more energy. In order to switch to a lower orbit, you must lose energy. In order to get to a higher orbit, you must gain energy. It turns out that losing enough energy to reach Venus is not substantially less difficult than gaining enough energy to reach Mars, at least not using ideal Hohmann transfer orbits.
Mars, you can land, go outside, build a nice sheltered place underground with a contained atmosphere, and maybe even make use of the sunlight. On Venus, if you use glass it'll be eaten away by acid, you can never go outside, and you can afford exactly zero failures in your habitable space, because it there's a failure you fall out of the sky and burn, or you burn and then fall out of the sky, or you sink a little bit before being crushed and burned, or....you get the point.