I have 3 rental properties and my accountant said I can save a little bit on tax prep if I can get my stuff into QuickBooks but besides that any advantage of using this software if only have a few properties?

Great for keeping track of expenses, income, etc...
Can't get it. You can have separate companies in QB as well. Also you can buy a program that interfaces with QB and print computer generated checks. I haven't "written" a check in years. I have about six or seven different "companies" set up in QB. Some are operating acct, liabilities acct (deposits), a savings acct, personal acct, a different company account, etc. My check writing program allows me to write checks from any company. QB is worth every penny.

I have 68 properties and am still using excel.

I think QB is overkill. I can get data into excel from my home improvement cards much easier than QB. And everything else (taxes, insurance, rents, etc) is going to be the same effort in QB as it is in excel.

I'm in the software industry myself and while I have no problems with subscription business models, I don't understand QuickBooks'.  $27/month for a product that used to cost $300 every 3 years or so?  That seems outrageous and I don't know if their "cloud enabled features" justify that mark up.

+1 on Excel.  It's also subscription these days (through Office 365) but the pricing makes more sense to me ($10/month for ALL of Office, not just Excel).

I use spreadsheets as well, as I wanted to minimize costs as much as possible when starting out. Maybe down the line it'll be worth investing in something else, but it seems like a good enough system makes it manageable just through excel.