Normally people who file returns late are also known to also not to their bookkeeping.

then pop over to fed ex to overnight docs back to the east coast.come back to my home office check e mail converse with my full time bookkeeper its usually how come we spent this on that and how come we did not make more on that deal LOLthen a little lunch or a lunch appointment usually with my banker.then afternoon I make the rounds looking at the new construction I have going on in Oregon.

In regards to book keeping, what are some things you learned or would give advice on when using quickbooks?

- there's really no reason your bookkeeper has to be local.  

or use a separate bank account for each property. never do data entry/bookkeeping again. your bank statements become your "spreadsheet."

When hiring someone for book keeping and financial tracking, do most people use the services that there management companies provide or do they have a single book keeper handle all properties. 

There are plenty of other real-estate oriented accounting software packages, but QB is still the 900-lb gorilla and you have enough complex stuff going on that the lighter-weight packages will likely not do everything you need.You can find a bunch of freelance bookkeepers (all of whom will know how to use QB) for way less than $400/m to help on sites like Upwork.

I think it really depends on if you want to keep doing your books or if you plan on handing them off to a bookkeeper.

QBO is good / necessary if you have a partnesrhip/ corp return of any type- but also it's easy to mess things up in QB yourself if you don't know accounting, so I typically recommend people use or have a bookkeeper who review type thing. 

I established an LLC for our rental property, but not to hold title or get a loan.Mainly for bookkeeping, and as a "management" company.