I have always been a huge Bosch fan. They make some great tools that will take anything. However I have been leaning toward Dewalt lately, but still will only buy Bosch for certain things. If you are comparing these two drills only, I would go with the Dewalt. Looks like the price is about the same. The Dewalt seems like you get a lot more. More Amps, More BPM, More rpm high and low and they both weight about the same. In regards to the Bosch running cooler than the Dewalt, I am not sure if it does or doesn't. Considering you are doing your won work, you do need something tough. But your not drilling into concrete every day, so not sure if that will pay a huge effect on the decision. Have you picked them both up in your hands? How do they feel? Because as you said you will be doing small jobs also and sometimes those are the most awkward positions for your body to be in and that’s also when balance and feel of a tool play a role. I wouldn't go with a 3/8" unless you will be doing a lot of smaller jobs. If you will be doing smaller jobs, over 50% of the time and spending a lot of time with these jobs, then a 3/8" might make sense. If your doing small jobs, why fight the extra weight of the 1/2". The 3/8" is 2 lbs lighter. A 3/8" chuck just seems so small. I would rather save the money and get some nice new bits or something else to make my work easier if I didn't do a lot of smaller jobs. Man I just confused myself.