help for upwind performance

hi to all

in the last months i have finally joined a group of a really good sailor here in rome...
i started do do some tuning work over my "82 h16 to have some regattas
and i have some answers:

mast rake:
i changed the shrouds this year with the new\short type to rake my mast but if i put the pin to the 3 hole from bottom i can't tight the jib enough (it's on the secon hole from bottom) so i must use the 4 hole for the shroud (minus rake) and can't go block to block without stalling the main.
me and my crew are about 145kg and the sails are about from the "96 but really almost news.
the problem is that i can't go upwind like the others, to have the same speed i must do a very low angle loosing a lot of water.
how i can go to the 3 hole to have more rake?
can i pin the jib to the 3\4 hole to achieve more tension?

rig tension:

tight or loose ?
some people here use loose rig to improve downwind performance it's really usefull?

thanx a lot
max