We boondock often in transit to our destination. The best way I know to find boondocking is the AllStays Camping app and the AllStays WalMart Overnight Parking app. The apps are fairly accurate, but sometimes you'll show up at a WalMart and there will be "No Overnight Parking" signs. I believe there are more places that are forced by their municipal laws to disallow overnight parking and the app doesn't get updated quickly sometimes. It's always better to call ahead so you don't waste time getting off the road to find a "No Overnight Parking" sign.
Yes, we have a Honda 2200 and easy starts on the air conditioners. The 2200 will only run one AC at a time and barely anything else, so you have to be very careful what you turn on. With our extended run fuel tank, we'll let the AC run all night when it's hot. The generator will use about 3 gallons overnight, so without the extended run tank, you'll be getting up in the night to refuel, which I've done, but I'm not a fan. Make sure you take a locking cable and run through the handle of both the generator and the fuel tank. We've never had any troubles, but we would prefer that someone didn't 'borrow' them from us. The Honda generator is so quiet that you hardly notice it running.