I have a 986, and when im sitting on the lights and try to engage 1st gear, sometimes its a bit tricky.
the thing is, it doesnt really have a pettern. sometimes its just fine, other times I have to wiggle the gear lever a bit for 1st gear to enter. it doesnt make a difference if its warm or not, it does it either way.
Could it be I need to check tranny fluid?

Also my clutch is slightly heavy. Ive had the car for 3 years now and it's always been like that. It's not extremely heavy, and it doesnt really bother me but compared to my other car, golf, it requires a bit more strength to press.
Is this normal on boxsters?

 

From what I've learned, our shift cables have crappy plastic ends; you could have one that is about gone. Just a thought. If you change them, check out Numeric.

 

If shifting into first is hard, try second and then first. Going to a synthetic gear oil will help too.

 

When was the last time you had the brake and clutch fluid flushed and bled?

If it has been awhile I'd advise you to do that or have it done. Supposed to be done every 2 years.

Ixnay on the synthetic fluid. If the car has enough miles just have the fluid replaced with whatever Porsche says. I've had my 02 Boxster 5-speed's fluid changed now a number of times and each time used Porsche fluid and the tranny is working just fine with now just over 275K miles on it.

 

Ive never had the clutch fluid changed. I need to do it. Regarding transmission oil, does it make that much difference in shifting if i change it? Will it solve the problem?