When you categorize each transaction using the software you can then create statements to understand your monthly or even yearly cash flow. 

The STR would be appropriately categorized as an "other passive activity", not a "rental real estate activity with active participation" as, again, a rental with an average period of customer use of seven days or less is not a rental activity under the passive activity loss rules.

It's very intuitive and has key functions that I really needed like the ability to quickly categorize transactions into categories that sync with your Schedule E for tax time, the ability to set up accounts for each property and sub accounts for specific things related to each property.

Notably, short-term rentals are categorized as non-residential properties.

It feels like Quickbooks to me and is easy to use, categorize, and see trends over time. 

Glen, I'm not aware of a way to automatically categorize items.

Yes, it is typically normal unless there is an agreement with the accountant where you will pay him to go through all your receipts, sum up the amounts and categorize them.It is confusing from your post because it seems like originally you mentioned not having your income and expenses properly categorized but in the end you mentioned providing it to him.

Notably, short-term rentals are categorized as non-residential properties.

also shivani these days the way I do it is I checked the inspection report and I would categorize it, will it require 30k-50k rehab, is it 75k-100k project ?

Properly categorize the expenses.That should help you with your bookkeeping.