1) it should loop around to upper flipper. Might have to adjust shooter rod to center of ball/adjust metal ball guide that ball runs along which can be a bit difficult/or check shooter spring...which I think was a 'green' one worked best. If you search this topic you will see a lot of info. on that.

2)Shouldn't be a hard shot...I never had that problem when I had the pin. Possibly adjust metal backstop. Hopefully others will chime in w/ answers. Enjoy the game and feel the power!

Great machine!

For #2 question, I have found that the eject shield (plastic red saucer) often times has one or both of the small fins broken off. Try replacing that, along with the suggestion above. You could also place washers between it and the playfield, which is a common trick on the IJ mode start saucer (search for those fixes as well).

There's mention of this(full plunge) in the manual. scroll down to second page,
http://mirror2.ipdb.org/files/2765/Williams_1990_Whirlwind_Operations_Manual_Br_With_Schematics.pdf

#1 it is supposed to loop on the SW inner loop, I just waxed mine and now it hits the right post on the jackpot ramp... So maybe your game is too clean
#2 mine also rejects about 2/3rds, but it always counts the skyway tolls even if rejected... Been like that since I got it and just take it as part of "my" game

As others have said...

1) it should loop around (sometimes mine loops around and sometimes it hits the post)
2) this never happened to me on Whirlwind, but I have had it happen on other machines (Jokerz!) but never thought much of it.

Regarding #2, you might try dead drop foam.

http://www.pinbits.com/index.php?main_page=product_info&cPath=17&products_id=131

Per the parts manual the stock WW shooter spring is the "silver" one - Williams part #10-148-1.

Hard plunge should take you through the inner orbit to the upper flipper. Stock plunger spring should be weak like TZ for the skill shot.

My saucer rarely rejects the ball. Probably needs an adjustment.