I might switch to cozy.co. which includes rent collection and post to various web site.

They have an app for the iphone: https://apps.apple.com/us/app/tenantcloud/id773281018Every plan includes the following: Accounting & Payments: Tenant accounting Expense accounting Automatic late fees Management fees Owner distributions Owner contributions Recurring invoicing Partial payments Joint & split rent payments Deposits & credits Invoice printing Accounting export Credit card payments Contacts: Unlimited tenants, owners, professionals Tenant notices Owner approvals Contacts management Roommate settings Owner portal TC messenger Property: Property specs Property gallery Keys & locks management Equipment & service reminders Maintenance request management Property import/export Loan & insurance tracking Property owner settings Owner reports Rental applications: Customizable rental applications Online application fee Tenant screening Online applications Property marketing: Marketing website Listing portal ILS syndication Message/tour inquiries Documents & information: Online leases Agreement template builder Account data export Cloud files storage Email & feed notifications Calendar & automatic reminders To do list Timeline & notes On-demand reports Amortization/depreciation trackers Other features: Customizable dashboard Easy navigation Verification process ios & android apps Online supportBelow is an independent review of this platform I found on the web...

If manual move to internet and web based storage software. 

It seems like a big gamble to guess at which option is more secure.

If the second unit does not have its own electric meter it should still work (worked for us,  we bought a home with attached apartment with our daughter who was a college student) also if the appraiser classifies the second unit as an accessory apartment or mother in law unit or casita instead of calling it a "duplex"   We're taking a gamble on a property right now where the underwriter said he believes the appraiser will be classify it as a single family with accessory unit (fingers crossed) this property is two separate homes with separate meters, so there's a chance appraiser will say the dreaded "duplex" and we wont qualify. 

I too would rather a one time fee program although under 10 units there are some free web based software.

Murray How To Make Big Money in Small Apartments by Lance Edwards (might be available for free from his web site, http://www.apartmentwealthinfo.com/, but Kindle edition is only $.99)Wheelbarrow Profits: How To Create Passive Income, Build Wealth, And Take Control Of Your Destiny Through Multifamily Real Estate Investing by Jake Stenziano & Gino BarbaroWhat Every Real Estate Investor Needs To Know About Cash Flow... and 36 Other Key Financial Measures by Frank GallinelliMulti-Family Millions: How Anyone Can Reposition Apartments for Big Profits by Dave LyndallHow to Take An Apartment Building from Money Pit to Money Maker by Craig Haskell (overpriced on Amazon...see http://www.valuehoundacademy.com/products/item25.c..., where it's only $20)Invest in Apartment Buildings: Profit Without The Pitfalls, by Theresa Bradley-BantaMany of these authors also have courses, Youtube videos, and podcasts you can learn from as well. 

The possibility of an error that could cost tens of thousands is not worth gambling.  

here is his web link: http://www.webuyhousesinconnecticut.com/I thought he had a great story and website.  

I'm willing to accept some risk, but I'm not going to gamble.