That is very encouraging to hear. Did he propose the 3 month trial contract or you guys? I thought of offering such a thing but not sure if it seems too desperate. Thank you for your comment.
In your shoes, I wouldn't be afraid to propose it - but only to a potential employer that you think is serious, but the work gap is a real issue for them.
If I was on the fence about hiring someone because I wasn't sure they would do the job and they offered to drop the price it would make me think that person is also not confident that they could do the job.
As a hiring manager, there is more on the line than the employee's salary. Making a bad hire can hurt morale, reduce productivity, and hurt the hiring manager's reputation. Having that extra money in your budget won't outweigh the potential damage that could be done.
During a job search you need to make those risks seem as small as possible.
In your shoes, I wouldn't be afraid to propose it - but only to a potential employer that you think is serious, but the work gap is a real issue for them.