I do my own bookkeeping.

Let's say, it costs you 1.5K to get your structures in place (holding LLC or Series-LLC, with or without land trusts, with or without separate operations LLC) and 0.5K per year (for maintaining the LLC properly, bookkeeping, lawyer and CPA, etc.) for a total of 2K.

While under state laws, I can run a PM firm without a license if I manage my own properties, I decided to play it safe to operate as a bookkeeping firm, so if questions come up, I am not collecting rent for others.But, there's not enough information here to give you advice on how to get started, and I don't know what your knowledge of accounting is.

Book keeping is very important.

Book keeping is very important. 

So I am looking for new software and wanted to ask for your thoughts.There are a few things I am trying to do:- Manage multiple properties through multiple LLCs- Keep track of invoices and payments from tenants (bonus points for accepting CC payments)- Automatically be notified of late rent payments and apply late fees- Give a book-keeper access so they can keep all the accounts reconciled- Be able to hand off data to my accountants at the end of the year- Online only preferred, but could download a client to my Mac if neededHopefully that’s not too tall of an order.  

I don't think I require any bookkeeping from them yet.How do you start the conversation and how do you vet CPAs?

I hired an amazing PM, a VA to help with bookkeeping and other business items, and a tax strategist.  

I haven't seen a lawyer yet that gets the tax language correct 100% of the time.Then, hire a bookkeeper. 

My tax guy has a bookkeeper in his office that charges $40 an hr.