If you have a ball valve setup, is there enough oxygen getting into the wort if you let it trickle out of the valve from the top of the bucket? This is what I do, and then I usually give the bucket a good shake/swirl once things are all sealed up. I have recently been having some 1.020 problems (multiple yeasts), and I am wondering if I need more aeration.
Last two batches I brewed went through 1/2" ball valves (older batch was 10 gallons that I shared with a brew buddy, we're both fermenting ~5 gallons). The newer of the two batches I didn't do anything extra to aerate it, other than let it run through the ball valve, via the silicon tubing, into the primary. In both the IC was moved around in the wort to help cool it faster. In the newer of the two, there was krausen in just a few hours, with airlock going well within 18 hours and going nuts not long after.
Depending on what you're fermenting in, you have options for aerating the brew. If you want something easier, put something into a drill that will aerate the wort. I made something to aerate my mead batches (while they needed it) and it works really well through a carboy bung hole... You can also use the beater attachment on an immersion blender, if you have one... Just don't turn it up too high. That would work in either the kettle, or primary.
I've also just poured the cooled wort through a funnel into the carboy before. Had solid results there too...
I would just try a few different methods and find one that works for you as far as amount of effort, and how soon your fermentation kicks off. Personally, if I can find a way that takes the majority of physical work out of it, I'd be inclined to try that first. I've done the 'shake the hell out of it' method, as well as pour into the bucket method. Both work, but the shaking takes more effort... If going into a carboy, if you don't mind the trub (or hot/cold break) going into the primary, just pour it through a large funnel... Put the bung in (use a 000 stopper in the airlock hole) and give it a good shake too, and you should be good.
Personally, I'll be going the route of via the ball valve for at least the next several batches. One of the fun things about home brewing, you can always change how you do a process if you find a method you like better.
BTW, kpr121, are you extract, partial mash, or all grain brewing? Getting stuck at 1.020 can happen for a few reasons... It's been stated as pretty common with extract brewing... It can also be from mashing at higher temperatures.