How difficult is it to join the military with a family?

Have you talked to a recruiter yet? Because a recruiter can answer all your questions and have the most accurate info.

Yes you get paid in basic and AIT. It depends on what MOS you pick where you go for AIT (Advanced Individual Training where you learn your MOS). It's probably unlikely that your family comes to AIT unless you have a job with a really long AIT. You get BAH with dependent rate as mentioned below it seems.

The biggest issue is going to be your husband and if he really thinks he can handle you being gone for months. I think basic is what, 11 weeks now? That's just basic. My AIT was 16 weeks and 4 days. If you think your marriage will survive you being gone and all that, then go for it. This is an Army perspective - I don't know about other branches.

Your best best is to go talk to recruiters from all services.

If you want any insight into being a woman in the Army, you can PM me.

Yes you can do it. Entry Level training isn't filled with only single folks. It isn't easy but it also isn't impossible. After entry level training at bootcamp and AIT you'll head to your duty station where you'll bring your family. Speak to a recruiter and they will be able to answer all of your questions.

First off, I was 27 when I went to Infantry One Station Unit training, so don't sweat your age. There are some Military Occupational Specialties that are exceptions to this following statement, but you will attend Basic Combat Training and Advanced Individual Training on Temporary Duty Enroute status and will not be able to bring your family until you get your first duty station, assuming it is one that allows them. That is most place, except some places like Korea.
Yes, you get paid at Basic Combat Training. Your recruiter should tell you what paper work you need to get your family covered by Tricare (military insurance for the families) and you will get Basic Allowance Housing with Dependents while you are in Basic and AIT. The rate will depend on the zip code of your current location. After you hit your first assignment, you will either get Base Housing or Basic Allowance Housing for the zip code of your duty station. You will also get a Basic Allowance for Subsistance if you aren't in the barracks and have access to the mess facilities.