@Steve T. First of all, congrats on the obvious success!
Of course I'm biased since I am a bookkeeper, but it's not a bad idea to outsource the bookkeeping and then you don't have to spend hours and hours simply learning how to use a new software. One of the great things about having a bookkeeper is you get the results of organized finances that help you optimize your business and rentals, as well as freeing up your time to manage your assets, buy more assets, or simply spend more time doing exactly what you want to be doing.
Stessa.com is a fairly easy to use online property management software that has basic accounting built into it that is pretty much set up for you, but I wouldn't necessarily say that it's super great. There are other property management softwares with accounting built in (RentRedi, Buildium, Yardi, etc.) but I personally haven't used them so I can't really give a good answer.
I love YNAB (You Need A Budget) for my personal budgeting and even business budgeting. While you can use it to keep your books, it is designed more for budgeting and cash flow management vs. bookkeeping/accounting. It's fairly simple to get the hang of and has some resources on YouTube and their website.
Of course Quickbooks Online is what you're always going to hear about, and while it's simple to use as long as you do everything right, there is definitely some nuance to figuring it out and learning all the ins and outs of how it works. This is what I use.
With 14 properties and doing it all on paper I'm sure you are very organized so best thing to do is to try and take the organization you already have and translate it into a software. Happy to help in whatever way I can.