I'm an investor, flipper, and property management company owner in central CT. 

As I’m saving up for my first investment, I would like to learn more about the industry - and it would be nice to earn some income while doing so.Are there any specific skills or knowledge I need to secure a VA side gig? 

Even if their Renters Insurance company wanted your insurance info, an insurance represetnative would be contacting you for it.7) You haven't stated if the tenant is current on their rent or withhold rent payments?

and frankly most landlords send a technician to fix things, not go there themselves, same goes for lawn care, usually you have a company that comes every week/other week, you do not need to be there.... 

Just because another real estate investor has success working with a particular company or person does not mean you'll have the same experience.

I imagine there is not much of a relationship with the turnkey service after the sale and I would deal with the PM and Loan company directly. 

Short of that, you may target employees of Canada-based companies with a presence in KC (this is easy to find on LinkedIn).

In looking to get better rates, I had an insurance company give me a quote. 

(you need to differentiate when a Mark Spain type company is running radio ads to attract business for themselves from it actually helping you out)4) Our TEAM or BROKERAGE has sold "X" homes! 

Get in contact with a 1031 exchange company during the transaction and roll it into another property perhaps.