I'm toying with the idea of starting my cutting right now. I'm attracted to the idea that they can get a head start. I typically start all my veggie seeds at the beginning of March and then depending on the weather have them out by beginning to mid May (mid May is obviously safer.)
Hardening off baby plants is always a little nerve-wracking. How much worst is it for a fig plant thats been growing indoors for 5 months? Someone mentioned it under Rich's propagation thread - something about how this transitional "shock" really set the plants back. Will it really undo the months I gained by starting early?? If its best to wait, when is a good time for zone 7 to start up the cuttings. 

My basic seedling setup is 4x T5 bulbs on each restaurant shelf with Alto 32W Daylight Deluxe bulbs. 

I'm starting cuttings now, and also curious about what issues folks have had growing them through the winter.  My guesses would be gnats, the daily chore load of watering etc, and having a setup with lights that can support the growth for an extended time.  Luigi, your lights sound like they'd do the trick just fine.   I'm hoping that by starting early I'll get a good jump on the growing season that's so short here in z5.   So far so good, direct potting my cuttings ala Harvey and Tim and taking preventative measures for gnats with Mosquito Dunk in the water.

My own opinion...
If you enjoy the challenge and it excites you to cater to your plants throughout the cold months, go for it.  I took care of nearly 150 cuttings two winters ago.  It was fun, but I would not do a large amount like that again.  Lots of gnats in the basement.  Having said that, I'm rooting a few test cuttings at the moment and will be putting them in various locations throughout the house to see where they grow best.  These are throw-away cuttings so I'm not worried about losing them.
Now for my special cuttings, I'm waiting to start those around March.  I would like to expose these cuttings to the outside world as much as possible when the first leaf emerges.  This will help with reducing acclimation time and sunburn.
The growth difference from starting cuttings now, opposed to March isn't that drastic (my experience).  By the end of summer, the spring cutting will have caught up with the winter cutting.

The shock will slow them down at first.  I would say 2 weeks to recover.  There are so many factors from one grower to the next that you have to keep in mind.  The indoor growing environment you gave your trees may have had more humidity than mine, and will adjust faster for example.  Your lighting, indoor/outdoor temps, etc all play a role in how fast a tree adapts to the outside world.

Where/what causes gnats? When I grew my veggie seedling last year I didn't have any problem I don't think (knock on wood.) Yes, it was TONS of babying but at least now I know I can do it!

I rooted around 90 cuttings last Winter and Early Spring and I agree with Frank..It is some work! raising and lowering your grow lights,Watering,Fertilizing,Fungus Gnats, and  etc....But I ended up with a Garage (now) full of nice  young trees....I kept thinking, I was going to loose more cuttings than I did....Would I do it again..Not that many! But, if I was just starting out, I think, I would keep the number of cutting to a more reasonable number. Oh yea, I couldn't help myself and I made some cuttings off my small trees, before storing in the Garage, so now I only have 6 cuttings started Sept. 23 outside and when it got cold I put these on my window sill and please excuse the dirty window....Good Luck!! :)

 

Do the rooting whenever your situation suits you.
I do all my rooting in winter because there is nothing else to do when between day and night temps are -15C to -20C in winter and then later there is so much to do in spring and summer.
 

I'm rooting some cuttings now with more on the way.  I have a greenhouse set up in my garage, after the humidity bin, they will be move to the greenhouse.  I have high intensity lighting in itand I can control the heat and humidity.  As spring nears, I will slowly start to drop the humidity and temp to match the outside environment.  Once the temp and humidity are dropped, and the weather says it's safe to move them out, they will be exposed only to morning sun to start then slowly moved into full sun over a few weeks.  This method has worked for me for years with an assortment of plant types, I'm sure the figs will respond with like enthusiasm.

Great plan, Scott.  I'll bet it works out great for you.

My advise is not to start too early. Also factor in if you plan on getting cuttings from UCD and from Jon. You will have all these different varieties in a couple of months. Don't overdo it now unless you have the room and the lighting to keep them indoors for a few months. It is a lot of upkeep and the head start might backfire when transitioning outdoors.
I understand how anxious we all get. In my opinion , it is better to wait

You can start anytime but be aware of the amount of light you will need to supply to keep the trees healthy and growing indoors.  I'm in zone 7a, I plan to start in Feb, so hopefully I will be transitioning to 1 gallons and then outside shortly after our last frost date.

Transitioning to full sun takes patience.  I take about 4-6 weeks to transition... or at least that's what seemed to work for me with little damage.  First week in full shade, 2nd week about 30 - 60 min early morning (or late day) sun, then 2-3 hours, etc.  And if the nights get too cool, the fig shuffle results.

Great point Phil . I forgot to mention the fig shuffle. One giant pain in the back. Bringing the plants in and out is something to be aware of as we are all anxious to get the figs out of the house.
Not fun

When moving outside time comes I will have a hoop frame set up to hold the 80% shade cloth Hershell provided.  The sides will face East and West so I can regulate the amount of direct light they get by rolling up the sides for morning and evening, weak light.  During strong light they will be under the shade.  Will increase the amount of direct light over some weeks. That's the plan anyways, if we make it to Spring with live plants.  

I have 19 cuttings going now and quite a few more on the way! This is the first time I have done them in winter a liitle more time consuming but not much going on outdoors anyway! I'm hoping to have a good fig garden soon!!

Here we must start cuttings in winter or else the summer heat will kill them. They are enjoying temps of about 27C this winter which is warmer than normal.

Hi luigiwu,
The choice is entirely yours .
You probably know about the eggs and the baskets . So, IMO, if you have enough cuttings, you could start half of them and see how you master the situation.
You would have to control : Humidity, heat, light , watering, no cold wold blow from opening doors or windows, no heat blow from a nearby heater .
As for the transitioning, if your artificial lights are good enough, you won't even notice anything . You can judge that on the color and thickness of the leaves.
Of course, if you loose patience and leave them outside full sun or on a cold night ... then they'll be toast like any other tree that would start growing too early.

But, if you put them in a shade, then half shaded position with temps night and day above 10°C/50°F, perhaps under a plastic sheet in the first week(s) (to cut wind and weight of the rain on the leaves), then, your cuttings won't be set back.
Don't forget to tie the stems to a stack as inside they don't get the wind hit, but outside they will .

At some point, you may notice that a late cutting will catch up with the early cuttings. Especially if you don't keep the pot well sized and the fertilizer dozed to the best .
But if you keep everything at the best, then that is worth it . Except perhaps, if you just consider the costs of the setup ...
But again, that is your choice and your judgement .
Your setup is 4*32W = 128 watts/hour just for lighting -acceptable to my opinion - + heating device .
What surface on ground do your lighting system cover (to know how many pots do fit under the lights) ?

I always start mine in winter...have 180 in cups now and still 200 or so still rooting all of which are new varieties.  When those are going well I will start some cuttings from my current plants.   It does take some work and you do have to be a bit careful especially with the water.  Once they are ready they will move outside to the greenhouse but it is easier here as spring comes early.  

I appreciate everyone's take on this question. 
Timmy2green, thanks for answering my gnat question. Is is possible for you to treat (including the soil) with permethrin before bringing it back indoors? I was watching a Praxxus youtube on this a while ago.

I don't because I have dogs and young children both which like eating bark from my pots. However I usually spray my tropicals w neem or horticulture oil before they come in.