My fiancee isn't too happy being taken out to dinner in the work van but I tell her its the "Money Maker" LoL.

I have a great life with my wife and kids and I don't need to spend a ton of money to have fun with them.If you're talking about investing the money you would normally put into your 401k into real estate and then earning cash flow now, that's different than just spending the money foolishly on new cars, expensive dinners, etc.

Take him to dinner at a place where you can sit down with a yellow pad and write out your investment goals together.

We drive modest cars because they get us from A to B and driving luxury vehicles brings us no joy, but we like going on vacation from time to time and going out for drinks and nice dinners occasionally.

Treat them to a nice bottle of scotch, cigar, and dinner and pick their brain all night! 

Meanwhile a financial advisor, who invited us to dinner a month ago, cancelled (before the restaurants closed) because he said they had to revise their strategy given the market pull back.

At worst, you get to hear how much of slumlord you are at Easter, Thanksgiving, and Christmas assuming Covid-19 allows for family dinners in the future. 

I'm perfectly happy to save $300/month in commuting costs and have dinner with my family every night.

Then they slap one another on the back and rush off to the next dinner party.

Ever have a tenant show up at your house, on a Sunday night, as you sat down for dinner, to try and "negotiate" a partial rent payment (already 10 days late) with the balance spread out over the next 3 months?