1. A payment processing system for processing a financial transaction between a buyer and a merchant using a mobile point-of-sale (POS) terminal comprising: a proactive support module configured to: collect merchant account information relating to a merchant account of a merchant with the payment processing system, wherein the merchant account receives payment information from the buyer via the mobile POS terminal, wherein: the mobile POS terminal is configured to run a register application configured to receive an input from the merchant indicating a product or a service for purchase by the buyer and configured to receive payment card information from a payment card reader coupled with the mobile POS terminal to facilitate a transfer of funds from the buyer to the merchant for the purchase, the merchant account information includes a particular plurality of merchant account attributes of the merchant account, wherein a merchant account attribute comprises at least one of a number of payments accepted by the merchant, a number of payment card reads by the payment card reader, a version of the payment card reader, deposit bank information, an amount of held funds associated with the merchant account, a status of the merchant account set up, or merchant profile information; receive merchant account login information from the merchant to access a merchant account support site; in response to receiving the merchant account login information: generate a merchant account context using the merchant account information, the merchant account context indicating a state of the merchant account; determine a merchant account problem at least in part by comparing the particular plurality of merchant account attributes associated with the merchant account context with a plurality of rules, wherein the merchant account problem is experienced by the merchant in operating the merchant account; generate a message for display to the merchant describing the merchant account problem and including a likely solution to the merchant account problem; and transmit the message for display to the merchant on the merchant account support site prior to the merchant searching for solutions to the merchant account problem; a knowledge database of a plurality of support tickets, each support ticket including a human generated response to a previous merchant account problem and a corresponding merchant account context at the time of the human generated response; and an analysis module configured to: retrieve from the knowledge database at least two of the plurality of support tickets; analyze the corresponding merchant account context for each of the at least two of the plurality of support tickets to determine a plurality of merchant account attributes and corresponding account attribute values or ranges of values associated with the merchant account context that indicate a particular merchant account problem; and generate a rule, for the plurality of rules, that indicates the particular merchant account problem, wherein the rule defines the plurality of merchant account attributes specific to the particular merchant account problem and defines the corresponding account attribute values or ranges of values specific to the particular merchant account problem.