I don't think Old English grammar was significantly more complicated than, say, modern German. In both languages you've got three genders (masculine, feminine and neuter) and four main cases (nominative, accusative, dative and genitive, plus instrumental in some OE dialects). OE did have "dual" pronouns specifically for two people, in addition to the usual singular and plural. I think it had a couple of different verb declensions (strong and weak); I can't remember what German has.
Modern English verbs are straightforward in the present tense, but I imagine the the number of semi-regular and irregular past tense formations are tricky for foreign-language speakers (and sometimes for natives). We also use three different present tenses where a lot of European languages would use the simple present ("I run"/"I am running"/"I do run") - I remember trying to pin down the rules for which to use for the benefit of a Chinese speaker. And even apparently simple things like the difference between "a" and "the" turn out to be more complex than they seem if you try to explain them to a Russian.
In some ways inflectional languages have more freedom in word order than English, because English uses it to replace the information conveyed by the case system. E.g. if you have "the dog bit the man" and want to emphasise who was bitten, you can't just reorder it to "the man bit the dog". An inflectional language can.
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