I like the idea of getting one under your belt to learn how to manage the "business" of real estate -managing the PM, bookkeeping, record keeping, etc. 

Hire a part-time bookkeeper locally, or investigate online VA (virtual assistant) that already have the skills and organizational abilities you lack or don't what to develop.They will put everything in a digital format which can be backed up in many different ways, and sent to your CPA at tax time.I speak from experience--life is short, and nobody is getting any younger. 

This really takes away the attractiveness of the "one stop shop" of Buildium, we don't need them for bookkeeping we use QuickBooks, they are really just somewhere that we were able to quickly list units and keep track of tenant files.  

My bookkeeper uses cloud-based Quickbooks.  

I put all security deposits in one account, and note the separations through my bookkeeping.

I have many years experience in accounting, bookkeeping, and doing tax returns for personal/small business.

My bookkeeper is with the same company as my accountant. $300 per month for bookkeeping.

That's exciting.My humble advice would be to make sure that you keep up with the bookkeeping.

That firm can then handle the bookkeeping (which you'll absolutely need if you choose S or C) and file the tax returns.

It's not that hard to keep track of and when it does get complicated hire a bookkeeper to help you.