I know what you mean as I thought about changing from the desktop version to the online version.

For me its: mail (duh), text, google voice, evernote, google drive, skype, logmein ignition (can remote control my PC desktop from my phone), Genius scan (create PDFs from photos), docusign ink (e-signatures) and notability (can sign PDFs but no e-signature verification).

With some lenders, the appraisal is called a "desktop appraisal" which means an automated valuation (similar to a Zestimate). 

And if you hire a bookkeeper using an online system makes sharing information so much easier.Here is my take:- If you are using a property management software other than QuickBooks than QuickBooks desktop or QuickBooks Online- If you are not using property management software than QuickBooks desktop- If you do not have rentals you can get away with QuickBooks Online.Are you a QuickBooks Addict yet?

Desktop.  

. - You can have unlimited files in Desktop and pay for discounted for multiple QBO filesBank Accounts:- Separate bank and credit cards account for each EIN- Do not go crazy and create one for each property.Reports in QuickBooks- Always use Class for each property for easy reporting- You can find line items not specified or unclassified with few clicks when using Class but not for Jobs.Accurate reports:- You will not get an accurate Balance Sheet by Property in QuickBooks Online- You will get very close to accurate Balance Sheet by Property in QuickBooks Desktop- When you view Balance Sheet by Class or Job report QuickBooks will give you a warning message that it will not be accurate.

When you select to change photo, does it bring up your desktop to choose an image from?

Using classes for properties can work in QuickBooks desktop, but I would not recommend it in QuickBooks Online since you are limited on the number of classes you can use.

:SBasically, I want to give back to this awesome community by creating a free desktop app (i.e. open source project for you techies) for all my fine fellow/fellowette investors, licensees, property managers, lurkers :p, I'm sure you get the gist by now.

@Shawn MorrowExcel can be great to track your income & expenses when you are first starting out.However, I find it that the accounting softwares are better when you have a handful of properties.My top recommendations for accounting softwares are1) Quickbooks(Desktop)2) Quickbooks(Online)3) Xero4) StessaBest of luck