Hey Nicholas,
Not exactly a software engineer, but I am a Python / Data guy.
1. I pulled county home sales in my target area, and called an API that converts address to Lat and Long. From this, I made a map that showed which areas had the highest increase in home prices, to show the "path of progress", ie: which areas are on the edges of the appreciating areas that might appreciate next. It point out a new neighborhood that wasn't on my radar before, but ultimately two deals fell through there and I bought somewhere else.
2. I built a real estate calculator that works probabilistically. IE: instead of saying maintenance is $200 / month, it uses a distribution, most months it's $0, while some months its $2000. It gives a range of outcomes for each investment: IE: in 10 years the 80% confidence interval for ROI is 2-14%. At some point I'd like to build this into a website, but html is such a pain the butt.
As for automations, I just use Mint, and then export the data and use excel to automatically categorize things - not a very Software Engineer type solution, but it makes my accounting pretty quick.