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Seems like the safe solution would be to go with separate sites and localize hosting for each as you mentioned. I just discovered Multilingual Press WP plugin (https://wordpress.org/plugins/multilingual-press/). Looks like it can provide ccTld and ability to manage all through a single WP Site with Pro version. I would lose the potential SEO benefit from local hosting, but efficient management might beat that. Need to dig into this a bit more. Also, WordPress Multilingual plugin (http://wpml.org) was recommended to me for "folders" or "sub-domain" solutions. I need to dig into this more, but I do feel better about using ccTld for each. Thanks for all the help and resources!

That helps a lot. Thank you!

#3 is a winner from my perspective, too. Nice feedback on this thread, everyone. Great to see!

Google updated their webmaster guidelines about a year ago to specifically frown on lists of keywords like this. See: https://support.google.com/webmasters/answer/66358?hl=en

I would still start with the sites that aren't ranking first. The more things you try to do at once, the less predictable the outcome is and the greater the risk of a negative impact. Start by moving over a few sites that aren't ranking that well. Gauge the impact. Do their rankings increase or drop? What about a month after you've made the move? Once you have a better idea of what the impact will be, you can move over a few more sites, and repeat the process. A piecemeal approach may take a little longer, but it reduces your risk and gives you a more predictable outcome. It also will allow you to perfect the process of moving sites before you get to the moneymakers that are already ranking well.