Most high-end property management software have the ability to set this up for you but there are also several companies that will bill your tenants for you and pay the utility companies in a bundled service, this will also help you ensure compliance.  

Does anyone recommend a certain software or perhaps an excel template to track cash flow for multiple properties?

.: There's no such thing as the perfect software.

What's the best software to manage the schedules and cleaning appmts?

.- Automation booking software to be transitioned, already has drip campaigns that the customer is entered into once booking a stay and reduces the management time to a few hours per month.- Membership programs (2 levels) that automatically rebook the member annually.***** Financials *****GOI 160K+NOI 75K+ (owner uses at minimum about 13K worth of time annually.  2022 was much higher)Taxes: 8KInsurance: 10KRent is current $600/night and is being increase in January to around $750. 

I asked him where the interest was, and if it should be reported on 2B of the 1040, and he said the software was not imputing interest.

@Brendan Flannery, I'm not a licensed real estate professional but I use RealEstateIQ software for my comps.  

We actually do it twice/month on the 15th and last day of each month.3) Management Fees are auto-charged by our software when a tenant pays.

In short, buy the software and then start running a search:Your city (and surrounding area)Just started a new job in the areaJust left a job in a different stateIs a VP, SVP, or C-Suite level individual (read: buying a more expensive home)By running this search, you'll get a list of a few dozen people who are moving to the area and are likely looking to buy.Good luck!

I have been using H&R Block software for many years.