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!

They likely also did not understand that ODC’s new business plan is still heavily dependent on significant rate cuts and rising rents; two things I believe are unlikely to occur. seems to me the play right now is to join in on the syndication that are raising this pref equity and jumping in front of the original investors.. maybe for you its like a stock market straddle play invest in the pref equity fund to offset your loss's you may incur in the original offering ( if in fact there will be any)..

We’ll see how this all plays out.