It can be done but usually going Windows is the path of least resistance for most non tech users.

I can agree that windows can be the path of least resistance because of legacy business softwares. But please don't even start to argue that windows is more easy to use than an iPad.

For a lot of professional things windows (Or Mac or Linux) is better. For data entry a tablet is a real pain. I wouldn't want to do accounting on an iPad for example.

How is doing small business accounting on an iPad, with a keyboard, any different that doing small business accounting on a Surface? You tap on the screen where you want to put data and type. Also, when using FreshBooks, which is what my comment was about, once you set up your customers, line items, and rates, creating an invoice involves about five taps and maybe typing in the number of hours/quantity, if it differs from the default of 1. That's it. I'm not sure how Windows could possibly make that any easier.

How does "going Windows" make doing small business accounting easier?

You have a lot of mature software available for that task.

I am looking at small business accounting. What are your thoughts on FreshBooks?

Personally, I love it. It is easy to set up your logo, custom web portal, customers, line items, and rates. Once you've got that done, creating an invoice only takes about five clicks. FreshBooks also emails invoices and reminders for you, allows you to easily accept payments electronically, let's you send satisfaction surveys to your customers, and gives you a weekly report on how much you've earned, how much you've collected, and how much customers still owe you.

I evaluated a bunch of other products, like QuickBooks, Curdbee, etc. but always ended up coming back to FreshBooks and have been with them consistently since about 2010.

Their customer support team is also great. I've only had one or two issues with the system, but in each case, they were quick to respond and help me resolve the issue.

The hardest part of running a small business for me is collecting money from customers, and FreshBooks makes that easy. FreshBooks allows me to connect with my customers in ways I wasn't able to before and it has reduced the process of billing to just a few clicks I have to do once a week; allowing me to focus on the services I provide instead of data entry and invoice tracking.

I hope that helps.