select transformed_tab1.id, transformed_tab1.level, count(tab2.id)
from
(select tab1.id, tab1.level, tm, lead(tm) over (partition by id order by tm) as next_tm
from
(
select 1 as id, 1 as level, '2013-06-07 07:03'::timestamp as tm union
select 1 as id, 2 as level, '2013-06-09 07:05 '::timestamp as tm union
select 1 as id, 3 as level, '2013-06-12 12:02'::timestamp as tm union
select 1 as id, 4 as level, '2013-06-17 05:01'::timestamp as tm union
select 2 as id, 1 as level, '2013-06-18 08:38'::timestamp as tm union
select 2 as id, 3 as level, '2013-06-20 09:38'::timestamp as tm union
select 2 as id, 4 as level, '2013-06-23 10:38'::timestamp as tm union
select 2 as id, 5 as level, '2013-06-28 01:38'::timestamp as tm) tab1
) transformed_tab1
left join
(select 1 as id, '2013-06-07 11:51'::timestamp as tm union
select 1 as id, '2013-06-07 14:15'::timestamp as tm union
select 1 as id, '2013-06-09 16:39'::timestamp as tm union
select 1 as id, '2013-06-09 19:03'::timestamp as tm union
select 2 as id, '2013-06-20 11:02'::timestamp as tm union
select 2 as id, '2013-06-20 15:50'::timestamp as tm) tab2
on transformed_tab1.id=tab2.id and tab2.tm between transformed_tab1.tm and transformed_tab1.next_tm
group by transformed_tab1.id, transformed_tab1.level
order by transformed_tab1.id, transformed_tab1.level
;