Geisha,
A lot of DH's have the same approach as yours. Perhaps a few hints:
Next year, gently suggest to your DH what you would like as a present? eg, "if anyone was looking for a present for my birthday, xyz would go down a storm". I'm afraid this is what I and my DH do to each other, and actually it works really well.
Regardless of whether you enjoy the spa day, can you tell your DH that you appreciated the gift and that he wanted to give you something nice. As he's basking in the positive praise, add that it would be a fabulous conclusion to your birthday weekend to put the xmas decorations up and go for lunch at the pub with the girls? Worth a shot...
I used to hate showing my body for massages, too. Then I realised that the poor masseuses got to see every shape of body, many of which were in a far worse state than I perceived mine to be. It's their job. They don't care what you look like, they are quietly working out what to cook for tea. However, I would shave your legs, at least for your benefit!
I can vouch for the benefits of a personal shopper. My husband is a Tommy Hilfiger addict because there's an assistant at our local shop who puts together whole outfits for him, and does it really well. He goes in saying he just needs a pair of trousers and comes out with three pairs, plus shirts and jumpers which all match the other.
Try online shopping, eg from M&S. Get clothes delivered in two sizes, try them all on in comfort at home, send back (or take back) what you don't like. Start with basic things where you can't go far wrong. Black trousers. A black t-shirt. A white t-shirt. A brown jumper. Ta-da!!! Try them on in front of your mum, if it helps to have another opinion.
And...congratulations on your 30th! Remember to smile lots!