I am planning to self manage as well and since there aren't many managers in my area I will likely employ a similar strategy once I decide to outsource the management.

Some lenders handle draws in-house, some outsource and depending on who they outsource to, this can become a real crunch. 

It depends on your goals, I would say outsource the management & hold the asset as nobody has regretted owning real estate on a long term basis. 

North Canton is a mess right now, they outsourced their building department and went way off the deep end with controls and penalties. 

Ideally you'd be there too (or a manager if you had one) as that is best practice in my opinion, but being remote you just have to outsource everything to people you trust. 

Keep plenty of reserves, and outsource the PM with a quality NARPM one.This is the way to do it in a high debt, low inventory era.

Only a few farmers are needed for food, outsource production overseas, financial and IT services will consolidate and go overseas, Entertainment industry takes very few people and can be commoditized by local youtubers very easily. 

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

Most bookkeepers won’t work in it if you plan to outsource it in the future.

You can outsource and automate all you want but when you run into your guests in the driveway and they want to talk you can't just walk away....your reviews will reflect that.I used $1100 and $437 as a real example.