Two questions that are unrelated, but for fun's sake..
If Venus were different how? More earth-like? Less inhospitable? Then yes, clearly we would go there first despite any greater escape velocity blah, blah. This is a simple engineering problem and not an insurmountable issue. Concerns over radiation on Mars etc are similarly non-issues, but long term living on a planet with lower gravity would eventually turn us in to skinny, little weak aliens. :lol:
If you ask me, I think going to either one without a long term strategy is rather silly and a bit like taking a vacation in the middle of the desert. "We're here, now what"? :ugeek:
In order for us to create a long-term presence on either one of these rocks we're going to have to plan and treat it just like the military treats its own logistical problems. One of the largest military bases in the world right now is out in the middle of the Iraqi desert and it couldn't be there without daily flights of men and material and supplies etc.. On mars or Venus we would want the base already built for us so that we could simply show up and turn on the lights. The way to do that is with cheap (relatively) specialized robots.. Robots that dig, robots that weld, robots that fix other robots, robots that power other robots and ones that do surveying, scraping, boring, tunneling, cleaning and on and on. I think we're headed in the right direction, rapid prototyping of parts, better computers, better batteries and energy solutions and better robots like spirit than we could have ever dreamed of two decades ago.. If we sent 5 box cars worth of such equipment to mars it wouldn't really matter how long it took for them to build our habitat, it would get done. The problem isn't getting there in the near term, we could do it now if we had to. The problem will always be what to do once we arrive and if the infrastructure is already present when we do then it's one less massive hurdle to face. Imagine if the pilgrims had showed up to Plymouth rock and downtown Boston was already built? This won't be beyond our ability in the next 20-100 years, but we do need to keep a focus on the long term goal and that is to make one or both of these planets a destination worth going to.
As for Venus having a moon like ours, I'm not sure if it would make any difference or not and since it doesn't, then why even put that card in the deck?