For 2010, I think it's finally time to get a bookkeeper. We're doing it in-house now, which means that it's always behind schedule and not as accurate as I'd like. In an ideal world, we'd like to...
Is this a typical use for bookkeeping?
Are there large companies that provide this service, or is it best to find a local freelancer?
What cost would you expect to pay for this service?
Are there any security concerns?
We use desktop-based accounding software, but can provide bookkeeper a logmein account to the virtual machine that hosts the software; sound like a good strategy?
** UPDATE: ** Google provides plenty of options, including Books2Taxes, which appears to outsource to India. Has anyone used these services?
What you described is what we do at my company (< 15 people). It works pretty well. Our bookkeeper comes to our place every 2 weeks to do the book. We also use TriNet to do payroll. If you are a small firm, you can also look into PayCycle (now Intuit) for payroll.
We use an independent guy who is fantastic but AccountTemps could also help you out. Since all the checks are printed at our place, we don't have many security concerns. We also trust the guy and setup some minor auditing to ensure things work out well.
To summarize, we have the following process for outsourced accounting/bookkeeping:
Bookkeeping is something no company should ignore. As a matter of fact, it's an area that can't be ignored for too long without major financial repercussions. To get a sense of why this is so, we need to look at what it means to keep the books and how this works and the impact this has on the operations of a company. This is not self promotion by any means it is just good information and should be taken seriously for financial well being and healthy cash flow. Seeing how your business is performing through the eyes of a professional qualified bookkeeper and record keeping system can make all the difference between success and failure Success and achievement in life comes down to the choices you make, choosing the right people, tools and equipment in order to reach your goals. Having the correct and up to date information is essential for you to make decisions confidently to manage your business activities.
Whoever is your tax accountant might offer this service.
If not, there are tons of "admin" services who will charge around $30/hour for this kind of work.
To answer some of your "ideal world" things specifically (cause I've had to do those things too):
Extra tip: When the bookeeper knows for sure what category to put things in, great, but we had problems where they would put stuff into the wrong category as a guess. Create a cateogry called "unknown" or something and let them stash things in there. You can go through that periodically (monthly?) and fix. Some things will be too trivial or one-off to bother training or fixing, but if there are patterns you can take the time to explain.
10Sheet is an interesting new service that supports bank account integration and receipt photo uploads, which is pretty close to the scanning feature the OP asked about. I believe financial reports are part of the package as well. They have a free trial, fyi. The subscription seems significantly less expensive than hiring a bookkeeper, though I would only try it out at first to make sure it does the job.