これはかなり単純な結合、合計、およびgroupbyだと思います:
SELECT t.r_id, SUM(t.work) work_sum
FROM tasks t
JOIN info i
ON i.id = t.r_id
AND i.date BETWEEN xxx AND yyy
GROUP BY t.r_id
その範囲に情報がないタスクにnullwork_sumが必要な場合:
SELECT t.r_id, SUM(t.work) work_sum
FROM tasks t
LEFT JOIN info i
ON i.id = t.r_id
AND i.date BETWEEN xxx AND yyy
GROUP BY t.r_id
その範囲に情報がないタスクに0work_sumが必要な場合:
SELECT t.r_id, COALESCE(SUM(t.work),0) work_sum
FROM tasks t
LEFT JOIN info i
ON i.id = t.r_id
AND i.date BETWEEN xxx AND yyy
GROUP BY t.r_id