I hear you on the small house issue. We three (me, DH, and LO) live in 800 sq. ft. (plus DH1, age 16) has an attic bedroom. We've had playdates here, but we seem to just trip over each other.
And, too, we are the least financially advantaged of my "mommy friends" by what seems to me to be a longshot. But we don't have any credit card debt or a car payment, and that helps me feel better. We do WIC but didn't qualify for SNAP because I have some savings and was honest about it.
I have a couple friends with houses that are so cute I don't like to go there. I know that is shallow, but it is the truth. I hang out with friends like that at places like libraries, parks, and LLL.
DH works hard but also really values his free time with us. I know that's the truly important thing, but I also know that we all compare our home, circumstances, etc. It is unavoidable (for me, anyway). I guess he might be able to pick up more work, but I would rather he be able to be with us on weekends and the occasional morning.
Can you ebay sell presents you get for a little income? I keep meaning to do this myself...
I am very new to the "friends" world also...I had to learn to make friends quickly for this new mommy life...I left a career to be a SAHM for a couple of years and had to crash-course my way out of PPD into having buddies and playdates. It was uncomfortable but DH was so encouraging and supportive that I did it.
Insurance companies suck suck suck. Hang in there, crunchy_mommy. And thumbs up to your for avoiding credit cards. 
Edited by McGucks - 9/18/11 at 8:06am
Follow Mothering