... The main question in my mind is whether I am missing something useful/valuable by foregoing one of these packaged solutions.
There is nothing that I do in Quicken that I couldn't also do in Excel if I were sufficiently motivated. When I was working, I didn't have the time and energy to create my own financial tracking system and now that I'm retired, I find I just have other things I'd rather do. Just like it's worth it to some people to pay a service like Blue Apron to do their meal planning and shopping, it's worth it to me to pay someone else a reasonable amount (which I define as under $100/year) to build and maintain a tool that helps me track my finances.
I will give you a list of some of the Quicken features I find valuable, but you will probably say that you have either already invested the effort to ryo, or that these are things that aren't relevant for your situation. Similarly, if somebody comes along and says that some other tool does everything I do with Quicken and it's free so obviously I should switch, I will just laugh, because the value of the time I would spend on having to resolve data issues and learn a new tool is worth far more to me than the actual cost of Quicken.
So all that said, here are the main features I use that I can think of off the top of my head:
- automatic downloads of bank, credit card, investment account transactions (I have a lot of accounts and transactions, this saves me at least a couple hours of manual entry every month plus it prevents typos that are hard to find later)
- automatic categorization of all downloaded transactions for tracking spending
- easy manual recategorization of individual transactions from the default with 2 or 3 keystrokes (e.g. to move a restaurant meal from dining to travel:dining)
- tax reports, especially for Schedules A and E. I also use the B and D reports for tax planning late in the year.
- various portfolio views help me decide what to sell and what to hold
- scheduled credits and debits
- lifetime planner
- track the cost basis for home and rental properties
- research (what year did we replace the windows? what store did we get that little table from?)
- as the treasurer for both HOAs where we own condos, I also keep the finances for each association in their own Quicken files and produce annual budgets and cash flow reports for the other owners as well as the report that is input for the HOA tax returns