Charisse's mother has an iMac and would like to get her software that will help her pay bills by writing checks. Leo says that QuickBooks is very popular. But it may be a handful. There's also Mac Personal Checkwriter. Understand though, that you'll have to get special checks that can be printed on your printer. Here's a complete list of the best check writing apps for 2019 - https://www.thebalancesmb.com/best-check-writers-4159967
Leo says that a security guru would say that under no circumstances should he use a public Wi-Fi network unless all traffic on that network is encrypted, and the best way to do that is with a VPN. It encrypts all the traffic coming from a phone or computer all the way to a VPN server, which could be something he runs in his home, or a provider runs for him. At some point, everything he does is on the public internet, but at least his traffic wouldn't be broadcast to the entire coffee shop.
He could use Quickbooks. They have software and a service online for a monthly fee, but this might be more than what he's looking to do.
Leo would suggest Mint from Intuit. It's free online, and instead of entering all the data himself, he would connect this to all of his accounts. It's completely safe to use because it uses the same backend service that all of the major banks use, Yodlee. So they have all of his banking information already anyway.