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I am really having a hard time teaching math it seems. And the math I'm having a hard time with is just in the 1B book! I'm having a hard time with the various ways to teach addition and subtraction when it is with a 2 digit number and also a 1 digit number. I decided to get the Home Instructors Guide and while that helps a little, it is still overwhelming to me. And makes me wonder if I need to add the text book too.

I'm not sure what to do to get over this hurdle. It is mostly my hurdle...my son might be just fine if I could just figure out exactly what I am suppose to do and understand it in a way that I can explain.

Don't feel bad-that is not easy stuff! Trying to teach 1st grade math our first year home ranks up there with my most difficult tasks thus far in homeschooling! I don't know that I'll be a lot of help; I ended up switching curricula eventually . Here are my thoughts, though:
1) Are you using all of the hands on activities in the guides? I think that was one of my mistakes.
2) How old is your child? If he's 1st grade, it might be that he's just not ready yet. If he's 2nd grade then maybe that's not it.
3) Are you just starting up after a long summer break? If so, start with a few weeks of review from the previous stuff he did.
4) Is this your first time teaching Singapore? It's certainly a different approach to any other math I've ever seen . Just give it some time for both of you to get used to the new ways of looking at math.
5) The thing that helped my son the most during that really rough period of Not. Getting. Math. was to just step completely away from the book for a couple of weeks. We spent a few days doing no math at all to give his brain a chance to rest ; and then we did a few days of math that was easy for him on the white board, or with manipulatives. Something to make it fun. Then we spent a week with the white board, gradually working into the concept that was difficult. Only about 10 mins a day during these stages. When I brought the workbook back out, he breezed his way through the previously tough pages and we went on.

We are about to start my son's 2nd grade year. I was already feeling stuck at the end of 1st grade. We ended the year a third of the way through the 1B book...so almost through the addition and subtraction, right before multiplication. So we have had a break this summer, with a few math activities thrown in the past few weeks. I think my son is probably getting it or figuring out his thought process that works. It's me though that is having a tough time making sure I am teaching it correctly, etc. Probably because to answer the question, for example, 27+8, I still use my fingers. Whereas Singapore teaches a few different ways to come up with the answer for an addition or subtraction problem.

To answer your questions:
1 - We did skip a lot of the hands on stuff. Yeah, that probably wasn't good. Though my son did great with the math in 1A, I just seem to be having a challenging time teaching some things in 1B. I ended up buying the home instructor's guide at my convention so I have that now too to hopefully help, though it is all still pretty confusing to me.

2 - My son is 7.5 going into 2nd grade.

3 - Kind of answered the summer break question above. I think I might just plow ahead and do the other topics right now (multiplication, division, fractions, time) and then it will swing back around to subtraction and addition and we can work on it again then?? We can also work on math facts during this time.

4 - 1A is the first Singapore book I started with at the beginning of last year (1st grade).

If your son is getting it, you're probably not doing anything too bad!! Hang in there; it will come. Singapore is just a really different way of looking at math, and, you're right-that can be the challenge for us, if we haven't learned that way to try to teach it. I do think the hands on activities in the guides will help. They do seem simple, and I think that's what makes them so good. It takes a concept or way of looking at it that looks very foreign in the workbook and makes it make sense. I will also say that teaching my children math has improved my own math skills!