Office Home and Business with Office 365 Exchange Online

We started Office 365 Essential 2 years ago aiming for the Cloud and Web services like Exchange and SharePoint. Due to budget limitation we kept using Office 2010 on Office Desktop PC. Now Office 2019 is released and Microsoft announced the end date for connectivity of Outlook 2010 to Office 365/Exchange Online.

Upgrading to Office Business Premium should be a natural way. But someone suggested purchasing Office Home and Business 2019. The initial cost is of course more expensive than recurring Office 365 subscription fee. But doing the calculation means break even after 3 years. If we can use Office 2019 for another 9 years like we did with Office 2010, this sounds a bargain!

We are an office of around 40 persons, all use Desktop PCs and need only Word, Excel, PowerPoint and Outlook linking to the Office 365 Exchange Online service. So feature-wise look feasible.

Can anyone share some experience or thoughts about pros and cons of running Office Home and Business version with Office 365? What would be some setbacks or limitations with such arrangements? Say in areas of usage, system administration, registration, patch updates, etc...