`group by`を作成すると、複数の列になります

irt_tlevel列の個別の値の数が固定されていることがわかっている場合は、条件付き集計を使用できます。

select 
extract(year from a.created) as Year,
a.testscoreid, 
sum(case when b.irt_tlevel = 'Low' then 1 else 0 end) as Low,
sum(case when b.irt_tlevel = 'Medium' then 1 else 0 end) as Medium,
sum(case when b.irt_tlevel = 'High' then 1 else 0 end) as High,
count(*) as Questions
from asmt.testscores a 
join asmt.questions b on a.questionid = b.questionid
where a.answered = True
group by Year, a.testscoreid
order by Year desc, a.testscoreid