Applying for a new Tier 2 with a dependent

Hello,

I am currently on a Tier 2 visa until August this year. My wife has recently applied for a dependent family member visa to join me in UK.

I should have a new job offer in April and will be applying for another Tier 2 visa (likely 5 year contract).

1. How does my wife go about extending her stay? Do we apply together, separately, in what order etc?
2. I should be eligible for ILR in 3 years time. Can I apply for a shorter Tier 2 visa in August with a view of applying for ILR afterwards? Would I save money by doing that?

Thank you in advance.

Your questions don't have complete/enough information....

1. How does my wife go about extending her stay? Do we apply together, separately, in what order etc?

If I understand it correctly, your wife has a PBS dependent visa till August? It's not mandatory to extend her visa with you in April if her current visa is valid till August. You can apply for her visa extension any time before the current one expires (you can apply for her extension after you extension/switching in April).

2. I should be eligible for ILR in 3 years time. Can I apply for a shorter Tier 2 visa in August with a view of applying for ILR afterwards? Would I save money by doing that?

I'm confused about this question. You mention you will apply for new Tier 2 around April with the new job offer but again you are talking about extension in August.

Thank you for reply.
Sorry I should have been more specific.

1. I am expecting a job offer in April but it won't be until August that I would be leaving current post and start a new one. The job is with the same employer but going up the rank. So, I guess I would apply for extension of tier 2 visa let's say sometime in June as it can take up to 8 weeks to process it and from what I understand add a dependant to the application?

2. As for the second question. My next post would be for 5 years which would be featured on my certificate of sponsorship. However, I have been on Tier 2 visa since Aug 2018 and from what I understand you can only be on it for 5 years in total. So, when I apply for extension this year would I apply for extension for another 3 years and then apply for ILR as I would have been on Tier 2 for 5 years?

You can hold a tier 2 general for 6 years in total. You won't get a visa past this cap even if your cos is issued for longer than 6 years total you have held a visa. Even if your cos is for 5 years, you will only get a 4 year visa max.