You should extend the stadium as soon as you are allowed. There's no point asking until you are doing well though as the financial outlay would cripple a smaller club. Build it up slowly. I expanded my stadium from 20,000 to 47,000 in 14 years. I was not allowed planning permission for a new one. That's the sort of time it will take, and even when I was the richest club in the world I still did not have the budgets that Arsenal or Manchester are given. Get your facilities improved immediately. You can do this at the same time as expanding, and it can cost a few hundred thousand to many millions depending on your level. Improve ALL facilities, including youth and training. Get your youth intake to exceptional which gives you a shot at the best regens.
Your staff numbers are terrible

As Bury I had 28 scouts, for example. 14 coaches, and numerous other staff positions. Most scouts were 20/20 where I could find them. But because you are a 'growing' club it will take time to build your backroom. Take it slowly.