While accommodation can be very nice in the larger towns and villages around the massif, styles and standards change in the road-less villages. Still, things are far from bad, with plenty of simple hostels known as gite and refuge huts. For a few weeks in high season, accommodation can easily run short.
Food is quite possible to get anywhere, but of obvious reasons, the more remote you get, the higher the prices. In the more remote places where there are nothing resembling restaurants, locals can usually be convinced to sell food or cook at a fair price.
Winter ends gradually the lower you get. Toubkal Mountain is usually clad in snow from November until June. Depending on your skills, the mountain can be climbed any time of the year.
Renting equipment is quite possible around the massif, the best place to do so is in Imlil. Available here are things like ice axes, crampons.
Several of the larger starting points into the massif have plenty of guides offering their services almost before you start asking for it. Few guides will cause anything like trouble, but talking to a few before you decide is a good idea, considering that you are engaging a person that will be around you all the day(s). Generally, the price for a guide is about 250dh/day, a mule costs 100dh/day. In addition a tip at the end of the trip is expected, no rule applies to how to how much this is.
There are many dangers in these mountains, but it is again a question of skills. Full rivers and flash floods, together with altitude sickness.
It is important to bring warm clothes even in winter, the best are items made from thin materials that breathe. A windbreaker is almost always handy. Also recommended are very decent shoes and sunglasses.