Changing employer: before or after current contract ends?

[srvg]

I work for a reputed university under Tier 2 General visa in the UK.
Due to lack of external funding for my projects, my contract ends in December 2018, but my Tier 2 visa expires in Nov 2019.

I got a job offer from a promising startup; I think it would take them at least 3 months to prepare to provide a CoS to me. Best case would be before my contract ends with the current employer and the worst case would be after my contract ends this December.

I would like to clarify the following:

1. Can I apply for a visa with the new CoS in mid-December while the contract with my current employer ends in the same month?

2. If the company can get the licence to provide CoS only after December then can I apply for the visa during the 60-day time limit to leave the UK?

3. Is it risky to wait for the startup to get this visa situation sorted?

(I also have an offer within the university in a different department with the same role. Even an offer from a well-established company which already has the sponsorship licence. But I am keen to work for the startup.)

Any advice, please !

Thanks.

[CR001]

1. Yes.

2. The '60 day limit' only starts when you get the curtailment letter, which can take a couple of months to get sent out.

3. Probably risky yes. Best to look around for something else too as a Plan B.

[srvg]

Thank you for your response, I just realised that I missed another question to clarify.
At the end of April, I complete 5 years in the UK under Tier 2 General visa, if there is a gap of 1 month without employment (while waiting for the new CoS to be issued or if the visa process takes longer), can I still apply for settlement?

[CR001]

There is no restriction on employment gap anymore. The 60 day limit gap has been removed.

You must however be employed at the time of ILR as you have to submit payslips and bank statements to prove your income.