Guesty is also great for communication with your cleaners - it sends them notifications for new bookings and they have a calendar they can view with their cleaning tasks.

4) How would you guys plan your daily tasks?

As our portfolio grows, it's necessary to develop systems to handle the routine tasks. 

The software allowed us early on to focus on implementing processes that work and team building rather thanfocusing on the nuts and bolts of how to accomplish common property management tasks.

Many are very anti rental units in their buildings, so I would make sure and diligently double check to see what rental regulations are like.  

This route offers economies of scale, as maintenance and management tasks can be consolidated.

As an Agent the task is short sighted, as a Buyer the task is long term, this creates a natural discrepancy.

Do one task at a time in each app so you can compare apples to apples.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.

It seems from your post his desire (problem) is he wants to get out of owning and managing residential real estate, and your desire (solution to his problem) is you are interested in taking on the task of owning and possibly managing a residential rental, so you just have to make the deal work for you both and if it doesn't work or his demand doesn't work with the numbers you've ran already than don't be afraid to walk away.

However, it is harder to scale SFH, buying 4 at a time is no easy task.