My worry is that financially I may not always be able to homeschool and will he adapt back into school or will he be less able to handle being back?
We homeschool now, and this is a real issue for us with the economy where it is and DH bringing home a healthy salary that might change if he had to find a new job. I like to think that every year we can do it, is a year closer to jr. high or high school where there are more options in our area. It's definitely a year to year proposition for us at this point.
The other very big issue is that DD7 is in a perfect school situation, great teacher, appropriately challenging and she is very adept socially BUT she will go crazy if her brother gets to homeschool and not her. I honestly feel that she is better off for now where she is but my two seem so jealous of each other.
This is hard. I have a 5 year old that started homeschooling this year instead of attending kindergarten. She is extroverted and very social. Kindergarten would have been mostly great for her. But last year when she went to preschool, she was bitter all year about her brother homeschooling. The previous year, she was delighted with preschool. Anyway, it's hard to know what to do. DD5 is extremely sensitive, as was I as a child. And I personally carry a lot of baggage about my own schooling! So that guided me quite a bit.
Anyway, I do think if you present it as a year to year proposition and say she has a really good fit this year that might buy you some time to try it out with one child. That's really hard! Good luck!