I've had several HOAs and just like property management companies most aren't worth it. 

Use softwares like AirDNA and Pricelabs to get an estimate of what you could be making and see if it's worth it.

Is the lot itself worth 10k?

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.

They can't print the envelopes cheaply enough to make it worth while, so I would still run the envelope through the printer.

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.

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

You'll want to enlist a CPA on this to assist you- Repeating the above for Cancun, since it's a vacation destination already, I'd almost guarantee you that you cannot write it off 100%In regards to travel, it's also important to remember that even if everything is used 100% for business, the IRS classifies business expenses being valid if they're "ordinary and necessary".

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