Benefits Include:Additional Cashflow, Hedge against Vacancy Expenses, Additional Cashflow to Pay off Rentals Faster, Additional Cashflow to supplement retirement income.  

You will need to be able to afford to supplement your tenants rent long term.

Whereas PITI would be $3800 and I would be able to use the tax advantage of ~1000/month to help supplement that.

The longer, more expensive reservations tend to come through vrbo.I would advise you to focus on 1channel and build up your placing there, while supplementing your rentals from other sources as well.

Usually they are allowed if they are used as a "supplemental" heat source.

I have one property in Melbourne and hope to purchase more to supplement my retirement.  

Either way you need your rent at market as opposed to supplementing your tenants rent every month.

Depending on the scale at which you plan to implement the software, I do recommend for large 3rd party solutions, supplementing some of the current software short-comings such as inspections, and maintenance asset tracking.

In that's the case maybe you'll need to supplement your pipeline to include some direct mail or wholesalers, etc.

I currently have an entire separate website, FB page, email, etc. simply as a means to supplement my bookings along side the major platforms.