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My first wasn't bad until the end when I developed Preclampsia. My 2nd wasn't bad until after she was born and then within minutes my pressures went nuts and I again had Preclampsia.
Now so far in my 3rd, we've been referred to a Perinatologist and baby girl is looking good. I have chronic high BP now and am medicated so that's under control and I've also developed GD which I am also taking an oral medicine for as well. This pregnancy is by far the most 'high risk' but the other two weren't bad at all until the end.
I talked to my OB before getting pregnant this 3rd time just to make sure it was ok in her medical opinion so maybe that's an option?

@rachiecakes: I did the first two times but the Perinatologist doesn't seem to think I will this time tho.

I have hyperemesis gravidarum, so both of my pregnancies were difficult in that sense. It was a little easier the second time around, since I had prepared some coping methods and knew better how control my disease after #1.

My second was difficult in whole new ways, though. Besides the HG, my first pregnancy was "normal," and both DD and I were perfectly fine after delivery. With DS, I had a whole list of other complications (including a velamentous cord insertion, growth concerns, partial bed rest, a PTL scare, cholestasis, postpartum placenta and bleeding issues, and DS had really bad jaundice at birth). So, in my experience, unless your complications the first time around are caused by something that is definitely going to repeat itself (e.g. like HG), there's really no telling how easy/difficult your subsequent pregnancies will be. I knew I would have problems with HG again in repeat pregnancies, but there was no possible predictor for all the other complications I had with DS. It was just luck of the draw that I ended up with those issues, and there's no indication that a third pregnancy will have all or any of the complications I had with my second.

I will say that pregnancy, in general, is harder on your body the second time around (especially if you have your kids close together), so you can expect that. A lot of complications, though, are unpredictable, so there's no guarantee that a first pregnancy predicts what a subsequent pregnancy will be like.

First pregnancy was not good for me. Sick until 28 weeks, From about 12 weeks on, I had constant swelling in my legs and feet (I could barely walk at times). I saw a Perinatologist every 2 weeks from 20 weeks on because of risk for Downs and possible heart arrhythmia (neither of which ended up being the case). Hospitalized for 4 days at 36 weeks for a severe kidney infection. Induced 9 days early because I was diagnosed with ICP. DD was born with high bilirubin levels and under the lights for 3 days. It took 4 months for my liver enzymes to correct themselves to normal levels (they were somewhere in the 600s when I delivered)
This time I have been nothing but boring (some Bleeding off and on at 15 weeks, but very strong hb and so my md pretty much said it was most likely placenta previa-by the time I had my ultrasound at 19 weeks the placenta had corrected itself, so much better this time around! I am shocked at how different one pregnancy can be from the next.