Good questions. For the first, they should try to concentrate in a particular area. Maybe not the same town, but perhaps the same county or the same state legislator district so they can at least get somebody elected. For the second, most of the people who sign up for this thing are libertarians and libertarian anarchists who seldom if ever vote Republican to begin with. So we won't be losing any votes by their departure. By contrast, if they do settle in a marginally 'rat state they may provide the electorate with a sizable enough minority to swing what would have otherwise been a two-way contest. In short, I don't think it will hurt anything and it does stand a good chance of picking up a couple of smaller offices with right wing conservative and libertarian candidates if they consolidate - small town mayors, city councils, state legislators, county commissioners and the sort.
There is another thing to consider, low population states are generally low population for a reason: not too many jobs.
How many of these free staters would actually move when the time came? They would have to give up careers, friends, and location-dependant hobbies. I think many would reconsider when faced with making all these sacrifices all for the sake of some lower offices. To actually turn a state into a conservative bastion and make it worth their effort they'll need a hell of alot more than 20,000. See post #9
You're half-right about concentrating on particular districts, but we're also attempting to avoid having all our porcupine eggs in one basket. As many as a quarter of those relocating are expected to head for the goal state's capital city, where they'll become the core of the eventual political party to evolve from the FSP migration- the FSP is NOT going to assume that role, avoiding alienation of existing long-term residents similarly inclined. We want to work with them and enhance their previous efforts, Not *show them how to do it*. THEY are the experts....
On the other hand, in at least three of the potential goal states, research has been done into previous elections and potentially winnable electoral districts, particularly in the Representative seats [this was a real easy project in Wyoming!] Whether one or none of those states is chosen for the initial effort, that research will NOT be abandoned simply because efforts will be directed elsewhere initially. Their time will come.