I'll share my thoughts, and hopefully some of the other moms will chime in. I don't think there's a lot of 'research' on this, just a lot of hard-earned knowledge from hanging around boards like this. 
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Your wee one is nearly six months. I suppose it is possible he's outgrown his dairy allergy - when was his last exposure? And what were his reactions?Â
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When I started doing elimination diets, oheightyearsago - the standard advice seemed to be to wait a minimum of six weeks between a successful elimination and challenging that food again. Later, the advice started to be more "wait 3-6 months." I'd err more in that direction, personally, if I were you. But then, I have a dd who still is allergic to eggs, and another who has outgrown her allergies (but they persisted 'til she was nearly 3). So in my experience, they've been more of a long-haul experience. With dd2, we waited six months between failed introductions/challenges. So, personally, I chose to wait six months between failed intros before trialing again.Â
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When breastfeeding, what I would do to challenge, would be to eat a small amount of the food the first day (say, a piece of cheese). If no reaction, then I'd go WHOLE HOG the next day. Dairy everything!! And see what happened. Even when the girls were older, the proteins would hit my milk and their reactions would be pretty clear shortly thereafter. Once they were old enough to direct-challenge, it was much easier as I could keep my milk clean and their reactions were even more clear (and quick).Â