How to work around the 100 callout limitation?



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Create a batchable class, and do as many callouts as you need.
 The 100 callout limit applies only to a single transaction, but Batchable classes can create millions of transactions. 

You could do this:
global class Do2999Callouts implements Database.Batchable<Integer> {
    global Iterable<Integer> start(Database.BatchableContext context) {
        Integer[] values = new Integer[0];
        while(values.size() < 2999) values.add(values.size());
        return values;
    }
    global void execute(Database.BatchableContext context, Integer[] values) {
        // Do one callout for each integer in values
    }
    global void finish(Database.BatchableContext context) {
    }
}
You would call this code using:
Database.executeBatch(new Do2999Callouts(), 100);
Of course, this is only an arbitrary example. You could use smaller batch sizes, base them off of records, or do whatever else you need to. 

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