QB Issue Resolution:

I think there’s no guidance on this because it’s really a personal preference. Some people will use the uploading banking feature as a tool to make data entry easier. Especially if you’re going to have repetitive expenses,  you code it &  the next time it downloads QB should remember your settings. Some people like to work more systematically going to date order, and if you want to attach pictures or documents to your expenses, it may be easier to enter them manually and add those documents as you go along.

Resolution for Issue 'Should I match?' available: Yes (Solved).
Source: Intuit Community forum.

Should I match?: this issue or error code is a known issue in Quickbooks Online (QBO) and/or Quickbooks. Support for this issue is available either by self-service or paid support options. Experts are available to resolve your Quickbooks issue to ensure minimal downtime and continue running your business. First try to resolve the issue yourself by looking for a resolution described below. If it is a complex issue or you are unable to solve the issue, you may contact us by clicking here or by using other support options.

Support for attach pictures
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Error Recovery for attach pictures [Canada]
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