Also, down the road (When you decide that running your own books is no longer fun and your time is more valuable than doing data entry and month end reconciliations) your system would need to be taught to an employee or outside accountant... it's a custom solution, which means that automatically the learning curve is going to be much worse for that person vs.

I've found a few, but they all cost a lot of money and I wonder how great they actually work.I'd like to automatically scrape emails from sellers on Craigslist and automatically send them an email.

Judges aren't allowed wiggle room to use common sense and the penalties are steep with an automatic judgement of 2X security deposit + court cost and the tenant's lawyer fees. 

Some relatively simple formulas can make it almost automatic and will suit your needs.If you want to get additional features support, my personal favorite cloud based accounting platform is Xero, but also Quickbooks is extremely popular with lots of customization options.Let me know if you have any other questions.

With goals like that, you will probably want to consider a shift to MFH somewhere in the equation.

Given the shift in education's environment (especially in my state) I recognize now the importance of multiple streams of revenue and financial independence.

Accounts can be linked so transaction shows up automatically and you can attach a snap of the receipt for record keeping.  

Is it noticeable to anyone else or is there a shift taking place in this Market?

My favorite is using the Intuit Self Employed App because it automatically tracks miles as part of the monthly price and updates your expense tracking.  

She's responded to say the husband (who I've not met) "works 12 hour rotating shifts, so I'm handling all housing inquiries & applications for our household.