Unfortunately you cannot show different content of custom html/text widget to different user roles, in the default software you can restrict to show it to some user role. 

What you want to achieve is considered as a custom code modification. 

Thank you for the feedback, I will look at having this developed.

Topic was moved from General Questions.

Arie Odendaal, you can create two widgets with the different content: one for the 'Free' and one for the 'Experts' membership type.  The only thing is that every user on the site has the 'Free' role assigned by default and there is no possibility to uncheck this role.  

All I can suggest you in this situation is to remove the 'disabled' status from the default role checkbox, so you could uncheck if for the 'Experts' users. But, before giving you the solution, be noticed that a user must have at least one role - so if you uncheck the free, this assumes that you check the 'Experts' role and vise versa. If you uncheck both roles - this may lead to negative consequences. Here is the solution:

Open the /ow_system_plugins/base/components/give_user_role.php file. Search for the following string:

if (in_array($role->getId(), $userRolesIdList) && $role->getSortOrder() == 1)

and simply comment the whole clause:

if (in_array($role->getId(), $userRolesIdList) && $role->getSortOrder() == 1)
            {
                $field->addAttribute('disabled', 'disabled');
            }