For the rental - I own two and if I was going to buy another, I would buy one that needed work. Additionally, as much as DH and I say we want to buy a house that is move in ready - we never do it, we always gravitate toward the house that needs work so we can put in sweat equity. I would find another realtor, ask around or just email a bunch to find one that specializes in investment property.
You are getting a lot of great advice (I've only read a bit), but agree completely on the property taxes and IRS, you really need to get those on payment plans.
I really posted in order to offer advice to your wife. When we realized we needed to turn things around, grocery bills and restaurants were one of the first things we cut. For restaurants, it was really hard to cut them out altogether. I started signing up for mystery shops which helped with our new zero budget. The trick was to stay within the reimbursement so I didn't spend anything extra. For groceries, we only bought what was on sale. If chicken was on sale, we ate chicken, if pork was, we ate pork. Same with vegetables, whatever was on sale, in season or on the markdown rack. For convenience foods, I only bought the items that were super cheap after coupons, like 50 cents cheap, free was even better. Most of it is crap yes, but because the amount I was willing to spend was so little, we ended up with very few convenience foods. I also used coupons for shampoos, soaps, etc - our budget was almost non-existent for those items so I bought whatever brand was cheap/free after coupons. Lastly, I had never had a veggie garden before, but I tried growing tomatoes one year because we loved tomatoes. Total overload and by the time we moved four years later we had a 20X10 garden. My daughter (1st grade to 5th grade those years) and her friends would go into the garden to snack on snow peas, blueberries and cherry tomatoes. They all wanted to help weed as long as they could snack also. Not sure if you have an area to garden, but even herbs are helpful. I started treating it like a game and at the lowest, we were spending $275 a month on groceries. I still do much of the same except garden, I don't think I could ever go back to my old habits. Good luck to you and your wife.