It's the leaving party's job to secure their exit without damaging the company.As you said, make sure you document roles and responsibilities of everyone, if property management is outsourced, insourced, who makes decisions, blah, blah, blah.

It is just better to outsource that job to a realtor.The only situation I could see it being advantageous for you to sell it yourself would be if it a complete dump and only a flipper would be willing to buy it.

If I do self manage, I would "only" handle the financial side (rent collection/turning units, legal), and outsource the repairs/maintenance/grass cutting.What would you do in my situation?

Most investors are simply committed to outsourcing that work to somebody else who rocks at it.   

Bottom line, there risk in either scenario but probably a little more if you outsource to a PM.

For fulfillment you can do it yourself to save money if you're broke, but ultimately if you want better response rates and focusing your time on value-add, then you'll want to outsource fulfillment to a shop that has economies of scale and can offer you great rates (see attached).

It will be really tough to manage the properties yourself working and commuting all those hours so you'll likely want to outsource your property management.  

I'm not handy and so, although, I self manage, all maintenance is outsourced. 

About a year ago, I started getting into publishing and have learned a LOT not only about publishing, but entrepreneurship, outsourcing, scaling a business and etc.

(out of state, so I'll have to outsource management)If the 10% cap benchmark I've set is not realistic w/in a day's drive from So Cal, what is?