Renewal feesOffice Supplies (e.g. stamps, envelopes)SoftwareGas/MileageAdvertising + Payroll12) Lawyer/Law office/Legal fees13) Accounting/Bookkeeping/CPA/Tax preparer/Tax advisor

For example, not many people like bookkeeping. 

I have used 2 accountants in that time, and they have cost between $1000 and $1800 to do taxes and financial statements each year (and I do my own book keeping). 

The three people you mentioned are all not necessary until you find a deal, and even then the role the will play is minor (depending on the size of your first deal.)They just need to be licensed in whatever state your business is located.As far as expenses for each Insurance Agent - $0 (paid from your premiums) check out nreig.com CPA - I assume you mean a tax attorney, which is different from say a bookkeeper who would monitor the transactions on your account and log them accordingly.

I'm looking for conferences to attend or even groups that meet (online, social media, or in person) specifically for bookkeepers/accountants that work in REI. 

If you are doing it yourself you can take off 10%True, in principle, from a book keeping point of view, but it means you are "working for free" then (i.e. you don't count the value of your own time/effort)

He's not in Indy but since we have a bookkeeper (me, haha) he really only gets involved at year end and so far, we haven't had any issues with long distance communication.  

I would give them a set date and if the security deposits were not transferred on that date immediately have an attorney ready to go to take action.Unfortunately, I have seen poor management companies mishandle their bookkeeping and accounting and were either unable to return the security deposit due to bad management practices, or simply embezzled the funds.

Book keeping update; taxes; and business plan.

I'm not REI full time but it sure saves me a ton of time, makes book keeping and tax prep easy and gives a professional feel to the tenants as I utilize online payments and applications.