You sound extremely knowledgeable on IT matters, and intimately aware of the directions software has followed over the years.

I am an old project engineer with a mechanical background who became self-employed some 14 years ago. I was tasked with being on the actual implementation of software packages over the years, the last real package being part of the Y2K fiasco.

Now, I am the sole owner & employee of a customer service business: In terms of how some describe it, I eat what I kill, so I have to find the work, do the work, and get paid for the work. I am the marketing manager, the IT Manager (with an outside support group), the purchasing manager, the office manager, bookkeeper, and I empty the garbage can. 

Some of my projects may go on for years, some for an hour. Transitioning to a new bookkeeping platform, which is really all Quickbooks provides, would mean hours of training, converting my files, etc. 

I do hope to do a partial retirement in about 2 years, at that point, I may transition my business to simply using a spreadsheet and a check register like Quicken. AT my size, paying over $100 per month for a software package that is non-responsive to the customer needs makes no sense.