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.

Can I bill them for book keeping?

Cons would be (I assume) higher costs due to separate loans.Benefits to a blanket loan would be cost and simplicity of book keeping etc..The second part would be;How would this affect any of us as far as the 'four conventional loan limit' for future purchases?

Is it better to wait until I have a full year of bookkeeping?

There are separate fee structures for each component (taxes/bookkeeping and legal), and you pay a fee up front and then a monthly retainer.