There isn't any "trying" involved--at least, for any honest purpose.
There is only "suggesting a site" (for review by the volunteers.)
I don't know how many topics you are considered an expert on (by your neighbors in real life, of course, I mean)--that is, how many subjects you can add to the sum of human knowledge in. Einstein (the other one) was famous as theologian, musician, and physician; Hoover was a world-famous engineer and classical scholar before he was president of the United States. But most people rest content with only a business interest and/or a hobby.
Well, all your sites are "related" if their content comes from a common source--that is, you.
In that case, it remains for the reviewers to determine whether all together, the sites count as one "historical record of the interests of a particular person" (that is, a personal homepage), or whether any of them count as "exceptional" pages on particular topics, worth deeplinking. (The rules for "related sites" really work the same as the rules for deeplinks to a single site: that is, normally, one listing--only in exceptional cases would multiple listings be considered.)
And the rules for "related sites" are basically, DO NOT TRY to get multiple listings: the penalty for breaking the rules can be to ban all the sites involved. (That's in the "submittal policies" you're supposed to read before making any suggestions.)
If, on the other hand, these "your" sites are not really "about" you, but are really created for pay for other people (or other organized groups of people, companies or clubs or churches, etc.) then you might check first to see if those other people already had websites (that is, if "your" site "about" them was unique), and if there was really more than a "business card" worth of "information" about the business--that is, if the site was "significant".)
And finally, you should know that some people have generated scads of "postage card" business "websites" which are little more than Yellow Pages advertisements, and gotten a very bad reputation spamming the Open Directory with repeated suggestions of them. And this is not a victimless crime--in fact, you might already be a victim! If the topics you're making suggestions to are spam targets, your suggestion might be buried in the spam, and the smell of the spam might be keeping editors from cleaning up the mess.
There's not really much any of us can do about this, except lynch the perps. But in some backwards cultures, even that's not socially acceptable.