Getting started again

I have started diet and excercise routines over and over and usually end up either physically ill or so sore it takes a week to get back to it. I am a 36 year old male, 6'0" and approx 250 lbs. I work a somewhat physically demanding job and this also deters my workouts at times. I am currently on an 1800 calorie a day diet and planning to work up to 4 one hour workouts per week minimum. For working out I have always used a combination of walking/jogging and weightlifting with freeweights(high rep per set). This method has helped me a few times to loose weight and tone up, but not since passing the 30 mark. Any tips on avoiding soreness would be greatly appreciated.