We’re still weighing whether to manage ourselves or hire a property manager, but I’m definitely leaning towards having a reliable team in place either way.Your advice about not taking on too much risk is a good reminder.

Lessons learned are related to the title process I use with sellers and buyers.

Unfortunately, that is an expensive time-consuming process.

If I'm wrong in my thought process like others I'm here to hear the best advice for all of us :) 

Is there an app that can streamline this process by synchronizing updates across all these platforms, thus alleviating the need for constant manual updates?

Staying involved in a business partnership while dissolving the marriage will rarely work.If you split the properties, I recommend hiring a good property manager.

Having a GC that will provide good documentation, itemized receipts, etc. will make the process much easier I've noticed. 

In Pittsburgh, where I live and operate, this would be a two to three-month process in front of almost all out local district magistrates.

Here is a link to 100+ bartending jobs currently hiring in Toronto. 

My process involves two steps.