Thoughts on bookkeeping software?

[Maggie L.]

Hi all,

looking for advise/perspective on software options for bookkeeping.  

A bit about my situation - buy and hold investor with multiple LLCs as well as a couple properties in my personal name.  Have been keeping track in a spreadsheet but my partner and I just bought our first duplex together (house hacking) so I'm now needing something that he can interact with (enter bill payments, etc) since he (understandably) is not interested in my cobbled together system.  I'd like something that would save me time (snap picture of receipt, automatically categorize expense, etc) and is easy enough for my partner to use (we don't share a computer so desktop only isn't an option) as well as give information to my accountant at the end of the year. 

Currently top three contenders are Quicken, Quickbooks (online), and Xero

My CPA works mostly in Quickbooks, but has experience with Xero and Quicken.  From a troubleshooting perspective he can do the most in Quickbooks, then Xero, Quicken the least.

Top priorities/concerns:

1) Avoid risk of Comingling while remaining economical
This is the big reason why I don't think Quickbooks online makes sense for my situation.  I have multiple LLCs, and I don't want to risk losing legal protections because something wasn't entered correctly or pay >$100 a month for multiple versions of QBO. Since I have been adding about a property a year I foresee QBO quickly becoming unreasonably expensive to follow best practices.

2) Useful user friendly reports
I have a couple rentals with my father who has physical conditions that limit his ability to use a computer, and this is only going to get worse with time.  I'd like something that can create useful printable reports for him to easily understand what's going on.

3) Ability to access from multiple devices

I'd like to be able to save time with mobile access e.g. receipt entry, and ideally multiple computers e.g.my partner can enter the sewer bill he paid via his laptop rather than me being responsible for all of the bookkeeping.

4) Quick system that works well for rentals

A frequent complaint I've heard about QB is its design.  It seems designed more for accountants (this is what I've heard from accountants), and a lot of the bells and whistles sound like they just get in the way for a simple situation like buy and hold rentals.  If this system takes more time than me entering things into a spreadsheet on my laptop once I've learned the basics then it's costing me money without saving me time.

5) Security

In a lot of ways this is the top priority.  To be more efficient I'm putting a lot of information (CC, EIN, Bank Account) into this system and want to know my data is secure.