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Other questions
@triview, while you are only commenting on the similarity of shared experience, the responses I have received from alleged Intuit team members seems as though they don't even read what I have posted. The general response has been to offer the advice that I have exported the CVS or created it from scratch from a non-QB source or downloaded it from an institution like a bank. The advice is that I need to make the CVS or delimited files conform to the Headers which the QB Import screen shows. I was advised to download a Template and edit the Exported CVS, without the "team member" understanding that the Exported CVS was created by my Company file in the exact same version of QBDT MAC!
To your other comments about moving to QBO - I already did that because this year, our non-profit is hoping to be able to hire low-end bookkeeping input p/t help and we have been using single license DT MAC version. The migration has been done fairly flawlessly; however, if you want to get me going, ask me how much I like performing 4-6 more steps or mouse clicks to do all the transactions I used to do in 1-2 actions in QBDT MAC. And boy do I love having to keep opening multiple Browser tabs, sometimes having to re-sign in each tab, in order to have an environment similar to my multiple open Windows within QBDT MAC.
I am kind of shocked, that if QBO is modeled after the QB Windows version, this is so clunky. I actually did a 6-week free course offered by NYC Small Business org. to train on the basics of QB. The course used an old Windows version, and when I started doing what I learned in my MAC desktop version, I thought there were a few features in Windows that were better. But, there is a general trend in the software industry to keep reinventing the wheel until it becomes completely flat, along with a movement to avoid most direct support of customer issues by providing huge libraries of articles, FAQs and Youtube videos (which ask for a review before you have seen 3 seconds). Most of these "solution" sources rarely answer my specific questions or completely solve the problems, and, of course, when you take the Survey to review the "solution" it turns out you are no longer signed in to QBO, and your Posting fails.
Since I will continue using QBDT MAC for a personal income company file, while continuing forward with QBO for the non-profit, I started investigating subscription pricing and came across FreeBooks and a few other alternatives. Depending what you are used to paying or how expansive your invoicing, form filing or check printing needs are, these alternatives may be good. I do not use or need e-invoicing, tax form filing, payroll or check writing within QB. I have taken care of payroll with FileMaker Pro and use File4Biz for W2s or 1099 NECs, and efile.form990.org or FreeTax USA for year-end reports and taxes.