If rates fall, you can refinance the 2nd without touching the 1st lien.I wouldn't plan for long-term financing with the Heloc as the draw period will term out at some point.

If you're an experienced real estate investor living in or around Springfield, IL, I'm looking for someone to provide advice and constructive criticism of my ideas, plans, research, and goals with.

Can the investor really hit the ground running with reno plans already in place as soon as the deals closed and investor takes control of the property? 

Insurance for not brand new home is very expensive. 

I plan to one day aquire apartment buildings for rental income.

Handling Maintenance requests and emergencies, Handling tenant disputes, Ensuring the tenants are properly insured (if you require them to), Marketing the property, Screening applicants, Handling the security deposit return, and a whole lot more. 

After the loans are eventually paid off, then add that to your investment plan.

He is now selling the property and the new buyer says she cannot find an insurance company that will issue her a policy because it doesn't have central heat/air.

The market is going to be a lucrative business if you plan to join the right team and use this forum as a Networking tool.

Don't tell him of your plans, don't tell him about your investments, don't ask him about his.