Your main concern at this time is to secure a regular income. This does not mean, however, that you need to stop trying to find a position that you will be happy in and that will utilise the skills you have acquired.
Employers still value people with experience in their market. It is important that when you spend time searching and applying for positions you approach the right people.
In a market where there are a large number of candidates applying for a small number of jobs, you must ensure that the companies you approach will be interested in your skills and background.
Focus on companies which will find your background in the insurance industry of benefit, or those that are using similar bespoke systems, which your skills will complement.
With 20 years' experience you may have a number of contacts still working in either insurance or the bespoke software market. Network with the people that you know to give you new avenues to explore in order to maximise your chances .
Finally, by way of enhancing your existing skills, which are now two years' out of date, you may want to look at some retraining. If you are looking for a support role you may want to retrain in a specialist area that will enhance the software knowledge you already have.
This may mean taking a salary drop initially, but should only be short term, once you have secured the right position.