1 a. What some tips to watch out for in a listing?
- If you want to buy, you should get a real estate agent. If you rent you just go over to immobilienscout24.de or similar. Old people do listings in newspapers, because they are not so familiar with "that internet thing".
1 b. Is it common for children to share a room in Germany?
I would say it is normal to an age up to 6 - 9. Kids normally then have their own room
How to make "Friends"? Although we found people friendly we were
curious how the locals would be with longer term interactions ie:
Dinner Parties, Drinking Friends etc.
I guess you will make most of your friends through a) work or b) sport activities. Join some club. If you are not into physical activities, there are also clubs for chess etc. Meetup.com is not really big except for the largest cities, but it is always worth a try.
a. We saw lots of Grilling Equipment in the shops is there a good
outdoor eating and cooking culture amount the locals?
You are right. That is a thing. People meet in parks to have BBQ, but as soon as you have a garden, you tend to host people there. Dinner parties are really common of course or just go out to clubs, have a bicycle tour together, etc.
Is getting a drivers license hard? What are the specific steps for
people with a US drivers license?
You can use a US license for 6 months in Germany (can be extended for additional 6 months), but afterwards you have to get the German one. According to that list, you have to do some theoretical test depending on the US state you mare your US license 
If you live in Germany are your children entitled to schooling?
Children have to go to school. Homeschooling is absolutely not common. You find international schools in bigger cities. AFAIK you might pay some administrational fee for schools, but the education itself is free.
Although I would probably be working remotely for a US company, is it
an issue to work for a local company if the opportunity comes about?
a. Is the paperwork straight forward or do I need a lawyer? Taxes: I
hear I would pay both German taxes and US taxes what are the
I think a tax consultant should be enough. (the next statements are with a lot of hand-waving) If you are working for a freelancer for the US company, you can pay the income tax in Germany, which would make it easy to accept local companies as customers. I have no idea how it works if you are employed by the US company.
What type of culture shock would be in store for a white middle class
american family from southern New Jersey face?
Thinking about the prejudices Germans have towards US citizens and reversing that, the biggest shocks might be:
If you ask a friend "how are you" they might actually respond to the question, not just saying "I'm fine, and you?". Germans can be direct and say straight to your face if something bugs them.
I hope that helped you to get some overview. You should definetly drill down each question at a time after doing thoroughly research.
Wish you the best!
 https://www.adac.de/infotestrat/ratgeber-verkehr/fuehrerschein/fuehrerscheinerwerb-usa/umschreibung-usa-fuehrerschein/default.aspx?ComponentId=35153&SourcePageId=48382 (German, sorry)