$1000 will only get you something second hand if you require turbo back and it will either be loud or restrictive.
I'd probably try to find something second hand that flows really well and stick a decent muffler in it.
It's more the fact that some things don't necessarily need replacing for a roadworthy, say a power steering rack that has a slight leak. but to the people that have no idea they will say a completely new unit is needed.
It really depends on where you take it. Some are more lenient than others but I'm assuming it'd be fairly similar to whatever state you're from.
One of the first quotes I has was $25ea to replace the LPG tags on my number plates. Obviously I want elsewhere and saved myself $1000 in the end.
List where you're from so we can make some recommendations.
I'd just stick the GTX35R on and wind the boost up. 500-600hp at the tyres is plenty for a street car that'll run 10s.
Are you planning on running E85?
If you only want 330 then just slap the turbo's on and away you go. Head studs and a new gasket will always be good insurance but aren't necessary at that power and boost level.
So I take it your planning on sticking to 98?
I'd probably go with the -9's if that's the case. You'll make your 330 with less lag than high flowed -7's.