I'm 31 I never met one person who moved to Lehigh acres under 50 years old. no jobs, infrastructure, commercial, etc and no utilities either. just a land play that a developer made millions on in the past 

That's not to say there aren't wholesalers here in Oklahoma, you'll just need to learn the rules to play

If you're not willing to work 7 days a week, work when others are out playing in the sun, forget it.

Decided to play it safe as it was my first deal and had to overcome the fear.

If he wants to retire I would definitely play up the continued monthly income side....You might also be able to get him to see that a lower interest rate protects him from a refinance out. 

So understand that while you can get a good deal, you are accepting a lot of risk by 'playing the game'.Finally - know that just because an auction lists a price - that is seldom the price something will sell for.  

There are numerous factors at play and your real estate tax professional is best positioned to opine on that.

It might not hurt to consider playing long-ball with them for now. 

I have played with AirDNA and heard of Pricelabs, but how accurate are these sites with their estimates?

If you haven't tried this yet I'd recommend playing around with some of the BiggerPockets calculators here https://www.biggerpockets.com/investment-calculators If you have a pro account you can use the calculators as much as you'd like, if you have a free account you do get a few free uses of the calculators!