In my experience as an agent (and long before an investor) people who are ROI driven and don't come with a passion for brick and mortar do not succeed in REI. 

I've got properties in (2) towns currently that are around 10k people in each town.

We have owned some real estate in other parts of the country and if you are in an A market you can do well, its the rural low appreciation areas where cash flow on paper looks great but in reality its not is where most people get hurt.

This deal was referred to me by a good friend, which means having a great network of like minded people is extremely important.

Each of those should know each other in a market as well.One thing to be aware as an out of state investor is that there are unfortunately people out there to take advantage.

I'm certain there are good strategies people are employing.  

I know many people have done it this way,  but two major parts I am concerned about are 1) how do you handle all the paperwork such as W2's, 1099's business records, etc. without meeting in person?

The majority of people I see on BP asking about syndication lack any track record of success, do not have sufficient knowledge of the property type specifically or real estate principles, financing and law in general, and have little or no capital.  

Although I’m guessing most people in this position would use Wordpress or something more customizable.

Some people I spoke with think it's their attempt to push their skip tracing  packages on you, but I cannot confirm this.Also, the text to lead percentage is .5, on average.