Yes, SW will investigate all income/capital you have as part of the means test. It will be looked on seriously if you try and 'cover up' income. Basically, you will probabsly end up with no Sw as they will decide that yours means cannot be determined if there is any doubt in their minds about anything. My advice is to declare all your interests/income. There may be an option to get Farm Assistance instead of Jobseeker's Allowance, depending on your circumstances.
with regard to the second question, this is really a tax issue to be sorted with Revenue. SW will only be interested in income from date that means test will be applicable from.