lots of "depends on" here on type, size, location etc - but seriously consider if bookkeeping/finances or Legal necessarily need to be in-house vs. outsourcing, lots of specialists for cheap and highly experienced to hire instead of a full-time employee doing these roles for you

Sometimes they're quick to outsource a repair, where it could have been done in house for 1/2 the amount.   

Especially those who make a living off of flipping and / or building houses, I would think this would give you great insight and control over rehabs & build expenses; whereas, when you outsource everything out to a GC, you have not access to the relevant details -- the budget, upcharges, permitting process, coding restrictions, etc.

Also you can learn the game, learn what the PM is doing, so later on when you decide to outsource PM, you know what questions to ask and how to hold them accountable. 

Outsourcing: As you start to grow your business you will need to start outsourcing.

But have been using outsourcely recently, because they have more people looking for long-term, permanent work, rather than gigs.. 

If you are worried about these types of conversations I'd recommend outsourcing them to someone on your team who is okay with them, then you aren't the bad guy. 

Let's just say, the value in PMing my own properties is really only available because of the control it allows me to exert and maintain things to my own expectations.And those expectations are also why, for me personally, even with checks and balances, outsourcing is not an option.  

We are going to charge more than outsourcing overseas but less than a typical US based co.What demand is out there for bookkeeping?

How much do you pay to outsource your VA to do your books?