Odds are a $20 pipe will not smoke as good as a $250 pipe. The more you spend on a pipe, increases the odds it will be a great smoker. This goes into better briar, better workmanship, the briar was aged longer, its from a better part of the burl, etc. The more expensive the pipe also means reputation. Dunhill collect what they do in part because they have a solid reputation (among other things). However, that does not mean the more expensive pipe will smoke better, it just increases the odds. There are plenty of $20 pipes that are great smokers, they are just fewer in between.
When going with a cheaper pipe, make sure the engineering is good. Make sure the stem fits against the shank properly, that the draft hole is flush with the bottom of the bowl and that the pipe is not too heavy. It should also be able to pass a pipe cleaner. This is harder to do with a bent pipe, but always check. Make sure it passes on a straight pipe as well. If not, then there is an issue with the engineering. Also avoid anything with a shellac type finish. On cheaper pipes, they can cause the bowl to smoke hot because the briar cannot breathe properly.
There is nothing wrong with getting an estate provided it has been taken care of and, in your case, is ready to smoke. This way you will not have to worry about restoring it yourself. Look for established brands such Stanwell, Savinelli Peterson (ask questions about the engineering), etc. Get the most expensive pipe you can afford, it will definitely pay off in the long run. Luciano pipes are an excellent pipe for the money, just avoid the bell shape they have at smokingpipes.com, they tend to smoke hot.
When I started out I was mainly into basket pipes. The three pipes for $60 and they were OK. I bought my first hand made pipe for $79 at a pipe show and the difference was amazing. Others have mentioned great pipes as well, its all good advice.
Welcome to the forums and keep asking questions. There is a learning curve to get the maximum enjoyment out of a pipe, but once you get the basics down, there is nothing else like it.
Mike