Since franchising takes some investment, I'm wondering if it's worth the investment or if doing a flip on my own to get experience is better.

Quote from @Louis Hamilton: The property is worth around 800,000 and has no mortgage on it.

In short, I’m trying to figure out if it’s worth pursuing an off-market seller financing deal versus getting a traditional loan and competing for the property on the open market.

That's bush league.Lastly, for what it's worth, I dunno why you're trying to die on the sidewalk hill.

Whatever you decide on your next investment, Little Rock is a strong contender worth considering.

That being said, there won't be any down payment required since you have equity (you're guessing ~55,000 but I wasn't sure if you were meaning the property is ballpark worth ~$175,000, or more than that). 

Are there any house at that price point that would rent for $1200-1500/ month with 20k worth of updating?"

Has anyone had any luck with this and is it worth it?

Your son is likely paying more than the property is worth, by definition, as the seller would almost certainly prefer a similar offer that was not subject to. 

Thanks.It’s definitely worth a conversation with your neighbor, but as others have pointed out, they might see it as you benefiting more than them.