Unless your dealers sell used stuff, you're not gonna get much bang from your buck trying to buy two saws for $1000. I suppose you could probably pick up a Stihl 250 or 251 and a 362 for that price, but I'd much rather have an 026/260 and a 440 or 460/461. Some Huskys to look at would be the 346/350/353 and 372. These saws are all widely available used, and personally I'd much rather buy a used saw from a member here with a good reputation than a used saw elsewhere or even a new saw.
For example, I currently own 10 saws. All but two came from here or the other saw forum. All run great, are high quality, professional grade saws, and all were purchased in good shape for much less than a new one would cost. If I had had a problem with any of them, I know that the great guys I bought them from would have done whatever they could to help me get it figured out.
If you wanted to go buy a solid two saw setup brand new from Stihl, you'd look at a 241 or 261 and a 461. Total for two of them is gonna be about $1500. Husky you'd shop a 545 or 550xp and a 372. Might sneak out for $1200-1300. If you insist on new, and draw the line below that for your budget, you're gonna have to make some compromises on quality.