two problems

Dear Collective Plant Wisdom:
I need info on two separate situations.
1.     Our church has 2 60-year old Italian cypress planted in front that need some shaping.  One is 8-10 feet taller than the other, and I meant to have it topped and shaped to match the other.  A gentleman in the church has said that will make the tree sprout off in different directions from the top, and it shouldn't be done.  Anyone have experience with this situation?
 
2.    I brought home 3 lovely jade plants from my mother-in-law's patio, and have put them on my front porch which is shaded, but receives indirect light.  I have only watered them once since I brought them home 2 months ago.  I also put them out in the sun for a few hours one day because we had been having so much rain, I thought they might need a little more light.  I confess I know precious little about their care, never having raised them before.  Now the oldest, largest one is showing brown "scabs" on some of its leaves, and I am wondering if I sunburnt them back a few weeks ago, or if I shouldn't have watered them, or if I'm not watering them enough.  Anyone grow these who can offer some advice on their culture to get them back looking happy again.  In fact, the two smaller varieties still look fine.
 
Thanks so much in advance,
Karrie Reid
Folsom Foothill Gardener
CA Zone 9
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