Hi Sheryl
Yes I think overweight dogs are more prone to anal gland probs as their digestive systems are perhaps more sluggish than a slim dog's. If your vet is willing to teach you how to empty Chloe's glands, then I would say go for it - we always empty our own dog's glands, not a nice job but once you get the knack, it's quick & easy to do.
As for what fruit to feed, well, whatever Chloe likes really - our lot like apples, banana, strawberries, melon, you name it really (no grapes though as eaten in excess they can apparantly be toxic)