I'm hopefully getting a puppy in mid-November. Nikon was also a fall/winter puppy, a pain to housebreak in the dead of winter with all that darkness and snow, but so far all I've ever known (I had Ana in Dec.). With Nikon, I crated him while I was at work, and for the first month he got let out twice. I would come home before lunch, and then a paid person came mid-afternoon to let him out and play with him and Coke for a while. Once he could hold it longer, I switched to either me going or having the other girl come just once during the day. We never had problems with him soiling his crate. He did take a long time to housebreak but only had accidents while he was in his puppy pen or having free time.
Then when I had Ana, I didn't have the option of letting her out twice, so I ended up taking her to work with me. I can't have dogs in my office, but my van is basically a dog kennel on wheels so I kept here in there (temps not an issue in the fall). I park in a staff-only lot that is on private property and patrolled by security, plus I lock the crate (locking the van doesn't do much if windows are open or cracked). Ana belonged to my breeder friend but I was helping to socialize her, so this arrangement was perfect because I work on a college campus. I was able to let her out several times a day and have lots of people petting her and I took her all over to practice climbing different stairs. Even though we can't have dogs inside I did sneak her in to visit several people, nobody cares as long as you are respectful of people who are allergic and make sure the dog doesn't potty inside.
I'm wondering which situation would work best for my new dog? I was thinking the second, since I can let the dog out more often and have more socialization opportunities, but then I was wondering if this would make a later transition to being crated in my home more difficult since the dog would be more accustomed to being in the van while I worked? Crated at home pros are the dog gets used to that crate in that environment which will be the more permanent; cons are that it's harder for me to get home and/or I'd have to find and pay someone to help me. Crated at work pros are I can let the dog out several times a day and use my breaks for socialization and exercise, don't have to pay someone to help; cons are it's more of a temporary solution until the dog is old enough to only need one break and be home, and the dog would have to get used to the home environment later on.