Bookkeeping Strategies - Prop Management, Landlording, BRRR, REI

[Will F.]

Hi, I invest and manage about 40 units + locally and a couple OOS.  

I was wondering how most of you do your bookkeeping?  I do a lot of rehabs, value-add properties etc.  Occasional flip houses, and a lot of construction on current long and short-term holdings.

I generally use Buildium software for the property management but I don't keep up with the books nor have the time to reconcile at months end. I sort of end up on excel at the end of the year importing statements and trying to categorize expenses, improvements, etc.  

Anyone have effective systems for managing all this or do you tend to outsource it?

Problems I forsee outsourcing:

I would find it difficult for a bookkeeper to know which properties to expense repairs for unless they already know my system.  It seems like whoever is doing the repairs (ie the prop manager) would be best at immediately inputting the expense into a software like Buildium or Quickbooks.  

So perhaps I need to DIY it as I go along or I need to hire someone in-house to help keep it up?