It's putting out lots of fires, managing finances like a hawk, keeping projects on time, in line and on budget, marketing the property & getting it through closing, and *then* doing it all over again - and that's if you're not doing any of the work yourself. 

If you only have one LLC and don’t need entity tracking, you could get a lower subscription and categorize your properties as ‘customers’, then units and tenants would be sub-customers.Simple Start would allow you to invoice your tenants (if desired through QBO) and produce basic reports. 

Nightly rates: Yes, but the benchmarks should also be lower.Year 2 turnaround: What strategies could we implement to project a higher ROI in our second year?

I would have appreciated someone pointing out how to more accurately project cash flow. 

I'm looking to finance the project long term in a way that is helps me create positive cashflow.

Has anyone done such a project before?

This is our "8 x 8 project" - there, I've said it out loud to remain accountable! 

It will familiarize you with the basic terminology and benefits.

Reporting is basic, but it tracks all rent inflows/outflows. 

You basically have no escape plan.