Older servers are better because there are plenty of 5* players on the market and many of those players go for 1-2T without bidding wars, If your on a new server (lack of 5* on the transfer market) then your always going to get outbid in auctions for good players if your playing on 35T a season.
If you can farm tokens then it's a different story and you should be able to compete with most token buyers and it will be easy for you to promote each season unless you get drawn in a league of death.