Well where do I start, short hair would be great and very much easier for you to maintain keeping smooth, straight, good conditioned and covering the grey. I would recommend going for a layered bob with a soft side fringe, the layers and soft fringe help soften square shape faces, just below the chin is a good place to start length wise as itís easy to manage. ...More >
You could have a smoothing treatment that lasts around 4 months and sometimes longer if you use the correct moisturing shampoo and conditioners.
The colour would be a re-application every 4 weeks just on the root area and by using a conditioning masque weekly and a blowdry smoothing lotion you will have the well conditioned silky bob thatís very flattering on all women of all shapes and sizes and easy to look after.
Good luck and I hope this is helpful?