If teams want to get off the bottom of the ladder they have to improve enough to beat the teams above them, regardless of the system you use. I understand what you are suggesting - give the bottom teams some wins to give them confidence - but I think it is giving them a false impression of their real standing and, with your system, creates a yo-yo effect of pushing them up one year and then reality bringing them back down the next when they have a harder draw.
Totally agree with the bolded sentence.
I understand your points after that but you are not factoring in a teams improvement from year to year, no-one can predict how or when that will kick in. The playing lists change every year and teams can also plummet on the back of retirements & long-term injuries.
I just don't see the point of having the top teams playing the bottom teams a second time because the result is a foregone conclusion already. At least under my system, you can see how much a team has improved or not relative to the teams that are normally around them.