I have Office365 and I think it's 100 bucks a year. Always updated and current, which is nice. I think there is a Office365 web version that is free. The Microsoft Onedrive online storage is included also.
I think Office is great for corporations but think it is a product much like ACAD, Adobe, and Quickbooks. The product works as is and has for decades. These companies roll out some small tool once a year to make their new subscriptions seem "worth it", and roll their customer service in with it to push you towards the subscription model. I say try out LibreOffice (it's free) and upgrade to MS if you decide it's needed. Like Jim, I have never needed it. Additionally I like to use open-source software as much as possible. It doesn't work as well sometimes, but I don't feel like I am helping some big company like Intuit lobby against making taxes a simple and reasonable process (I really don't like Intuit).
“It really doesn’t have an Outlook analog, which is an issue.”
I use Thunderbird for my personal email. It has much, but not all of the Outlook functionality. Apparently there is now Outlook.com, free to windows users, which is (said to be) very much similar to the full version. I might try that.
For the most part in life, you get what you pay for. I find it funny how the vast majority on this form like to slam the bottom feeding low ballers in our profession but then whine about paying for the services of others. While there are areas that I've chosen to utilize a free or open-sourced alternative, the discission is usually based on ROI and/or features. There are some open-sourced applications that are just better than their commercial alternative. I also don't mind going open-sourced for things that I rarely use t such as image editing software packages.
I'm using Office365, the business standard addition which around $150 a year. With it I get all of the office suite as well as Teams and 1 TB of storage. Just the 1 TB is worth it. I keep a significant amount data in the cloud so I can access it from anywhere without having to go through my VPN. I also use it for data transfer to my clients. All of that for less than one billable hour a year. Seems like an ROI and feature win to me.
I just go with the Office 365 subscription because (IMO) it is not an expense to worry about and I am already familiar with it. I think the cost is around $100 bucks a year.
I will say that the Google analogs are pretty decent and getting better. Pretty much anything that I need to do can also be accomplished in the Google suite of products. Like Office, Google allows for collaborative access to documents for editing.
I am not a business owner, but have used Open Office for a number of years without issue. I'm back in school now going for a bachelor's from UMaine, so I get a free access to Microsoft office. I use that now because it's there. But once that's over with, it's back to Open Office.
I'm in the camp of open software when possible. I bought Microsoft office like 8 years ago, tried to load it onto a new computer for school, and Microsoft stole it from me. THey will not allow me to install MY property on my computer - it's forced subscription now.