How to get tenants to pay online? (Especially at a large complex)

[Howard Rubin]

Hi all, I own and manage 300 units (made up of a few large apt. complexes).  I am in the process of considering property management software and wanting to hear from others how they got a good majority of their tenants to switch to paying rent online instead of writing checks.

As we have rental offices at our properties, most tenants just drop off handwritten checks there (we even have a mail-slot for after hours), so there isn't that much work involved.  Our tenants are more blue-collar, some are older, some don't speak English, they aren't young tenants in the "luxury" market who are itching for this service, and just not sure how to know going in how many will actually pay online.

When speaking to the software companies, one salesperson sold the idea of being able to add an additional revenue stream by charging tenants a few dollars more for the convenience of paying online -but- I have seen people recommend, in other posts here, raising rents a little and then offering a $5-$10 discount to incentive them to save money and pay online (the completely opposite strategy).

Would love to hear from others, especially those at larger complexes, how difficult and challenging it was to convert a majority of tenants to pay online?  How long did it take?  Did you incentivize, charge more for convenience, etc.... would love to hear all experiences on this.