Advice on going for ILR vs Tier 2 extension for a year

[spai77]

Hello all, I've just joined the board today and apologies if this is a trivial or repeated question but the timeline I have to make a decision is compressed, hence I'm posting here. I'm getting conflicting views from the people in my Visa department and some other colleagues who are considering ILR.

Here's my case:
1. I work for an IT services provider and I entered the UK in September 2013 on a Tier 2 General Migrant visa, which was initially valid for 2 years.
2. My family joined me 7 months later in April 2014 and are registered as my dependents
3. After 2 years, I've had one extension in 2015 for 3 years, which runs up till 11th Sept 2018
4. As it stands, my 5 years will be complete in Sep 2018 whereas my family's 5 years will complete in Apr 2019
5. I have a business trip coming up in end Jul 2018 for 3 weeks (till mid Aug)
6. I am eligible for another extension (of a max of 1 year) or if I apply for an ILR, my firm apparently pays up to the amount for the extension with the balance out of my pocket.

Right now, I'm confused with the multiple choices. Would really appreciate some guidance here or even a new option. Given my trip coming up in July, I'm not sure how the timelines will work out. I've also heard that the Home Office is going through the Windrush applications so ILR appointments may not open up till end July.

1. Should I go in for a year's extension for the entire family and then in Mar/Apr 2019, apply for ILR for all of us? In such a case, if I get a year's extension, will I have to wait till the year is almost over before I can apply for ILR?
2. Should I go in for ILR for myself + extension for my family now, and then in Mar/Apr 2019, apply for my family's ILR? Will it be more problematic if I apply for my family's ILRs in isolation?
3. Any other option that you all recommend given this situation?

Many thanks,
Sachin

[CR001]

1. You can apply now and they can apply for an extension of their PBS Dependent visa and then apply for ILR when they meet the residence requirement. If you choose to extend for 1 year, you can then apply at anytime once everyone meets the requirements.

2. No issue to do this, many have done it.

3. Not really. It is not as hard or difficult as you might think.