What are the benefits and challenges facing those who have retired or are planning to retire in Germany?

One of the greatest challenges is Medical coverage. There are also issues with how one can receive their retirement pay. Finally, it is vital for those who have medical issues upon retirement plan well in advance in receiving the VA medical review.

Good luck.

MSg Ewing. Really going to be determined by where you retire to. Stuttgart, K-Town, Heidelberg Areas you should find it easy to find work. If you aren't there on some kind of Status of Forces arrangement then you will have to be an ordinary resident (this should be your last resort) and subject to the full gamut of German Taxes. You can look for a GS position but they have been limiting that to 5 years in country then you have to repatriate. The military will pay for one move to your home of record or a final destination so use it wisely. If you have IT Technical Skills and an active clearance there are many opportunities for you. You will want to qualify for technical expert status accredidation (TESA), this puts you on a SOFA type of work arrangement and gives you full commisary and BX privleges as well as if you are a contractor, there are tax free benefits as well. The biggest issue for you will be schooling for your kids if they are school age. That can be expensive if they aren't just going to a local german public school. I assume they are going to a DoDDs school, so if you want to keep them in that school it runs about $26K a year per child. There are options to cover the costs with both contractor and GS position, so do your research and make sure everything is spelled out in your international assignement agreement. Finally, read The Art of the Deal and remember everything is negotiable if they want you.

I know several people that got out in Germany, then wanted to come back to the US within a few years (six at most) and had to pay their own transportation to do it.
I would suggest that it is not the best idea.
You gotta be really, really sure that you never want to live in the US again, and even then, I wouldn't do it.