Beautiful, long hair, capable of being worn in a feminine style would be great, but as you mention, it can be a problem socially and in business for many of us. Suddenly growing your hair out after fifty years of having a more conventional hairstyle would raise eyebrows for sure.
On the other hand, maintaining a conventional hairstyle and wearing a different colored feminine wig when presenting as a woman has its up side. Maintenance is much easier, there are no social or business problems and most importantly, the different hair length and color can go a long way to concealing your identity in public. So, that's my choice.
