For whatever reason, I've got a hard and fast rule for myself - only learning languages within the Indoeuropean family... I think... well, it's partially just a question of quantity vs quality. I've already got my toes (or languages) onto a few branches (so to say), so whatever new language that catches my fancy is going to be a lot easier than if I didn't know any of its relatives. Well, Polish is practically rushing along, because so much vocabulary and grammar is similar... Or it would be better to say, so little vocabulary and grammar is different from my native Russian... So, yeah, I'm not getting younger, and if I have this gnawing desire of learning more and more, sticking to familiar waters (which are still brimming with fascinating oddities) is very useful... Unfortunately I feel like English isn't the best starting off point even in this sense. There's a lot of borrowed vocabulary, but I've found it not very helpful at all when transitioning to the grammar of any other language, including German. Mainly for the cases and genders, I guess, without which you won't get anywhere. Oh, and, of course, the fact that German actually tends (or tended) to stay away from Latin-based vocabulary, instead preferring to invent its own compounds (like Fernsehen instead of the Latin world's TV). I've at times found it useful to instead look at translations in Russian because even though they're more distant cousins, something in the way words are formed makes more sense (although a TV is still Latin-based in Russian)...

I guess that doesn't help you any. Well, I've long thought that if a person could be persuaded to get interested in it, Dutch would be an excellent middle ground between English and German. Both in terms of vocabulary and grammar. But it's really hard to get enthusiastic about it because of how little it is in the public consciousness, I guess.