This points to economic weakness.

Yes, it is a numbers game as well, but long term success comes from relationships, not taking advantage of someone one time, because you caught them in a weak moment.I think it is great you are taking the meeting. 

Just too much political BS going on if you as a landlord aren't perfect.Other thing, never use the word "sorry" with a tenant - They can sense weakness :)

My biggest weakness going into the program was estimating repairs and working with contractors.

They are all highly different markets with very different rates of returns and strengths and weaknesses.

According to CAR’s chief economist, Leslie Appleton-Young, “With the shortest time on market in recent memory, an alarmingly low supply of homes for sale, and the fastest price growth in six-and-a-half years, the market’s short-term gain can also be its weakness in the longer term as the imbalance of supply and demand could lead to more housing shortages and deeper affordability issues.”

Unless you are 100% transparent with your brother and you are open about each other's weaknesses and strengths I would not do it.

Also, I wouldn't conflate thin syndication deals with a market being strong or weak.

Zero risk of loss.Find a weak seller that doesn't know what his prop is worth, tie it up with $0 in escrow and walk it around.

The reason trades are lacking now is because millennials are weak and lazy, and they think a college degree guarantees them a cushy seat in a corner office making a bunch of money.