I have several AirBnB properties in Dunedin and find that it's a mix of vacationers, people moving to the area for work or retiring, and people visiting aging parents. 

Me paying it off in my ideal time frame (8-10 years) coincides almost exactly with him being between 65 to 70 (ie retirement age) so I know I could make more money by delaying the payment, but I would rather take care of the man who has taken care of me my entire life first!

Chris, unless you are at the retirement age pulling funds from your 401k will be considered early distribution, which will result in taxes and penalties (both on state and federal levels). 

I started at a young age as well - mid twenties. and found it difficult to connect with active investors when I didn't have much value to add.

So buy them in your personal name, then age out the oldest that you have financed or the ones with the smallest balances to the Sub S and get commercial / portfolio financing on them at the best terms you can find.

Im 19 and want to see how much i can accomplish by the age 30.

Old houses have cast iron pipers that will disintegrate (because of age and/or foundation shift).

At age 20 nothing else is owed into the policy.

Not everyone optimizes their life for financial efficiency and long term wealth, especially once people reach a certain age in life and values change. 

I just had the roof inspected and confirmed there are no signs of active leaks, but the age shows from the exterior, and the company sent out their inspector who commented on its appearance.