Simpler, easier, and still functional.

Once you have a short list, get an account with each one and run them through the wringer to see how they really function.

That is the purpose and function of a properly drafted and filed correction instrument. 

My low-level intellect can't seem to function on your level.

Part of the reason I want to flip is A) make something functional and useful again and B) use the artistic side of my brain to create beauty.

I would make a separate entity if the function/assets of the business are different than that of your current entity

Use caution as an anything not functioning or highlighted for repair will need to be disclosed. 

I can quickly create bank accounts for each property, the categories for tagging your transactions align perfectly with your Schedule E for taxes and I can do all of my tenant related functions like tenant vetting, lease creation and collecting deposits and rents.

A number of people have asked this and if you use the search function, you can see replies to those posts. 

I know cost is a factor but think about overall functionality and does it do the 7-10 things you really need?