Being able to use real estate to offset taxable income requires some sort of participation on his end.If he wants you to be the boots on the ground, it will likely be hard for him to reduce his taxable income.

Compared to STRs and LTRs?

Just make sure your personal use doesn’t exceed 14 days, or 10% of the rental days, to maintain its rental status for tax purposes. 

It's still possible to BRRRR now, but the deal has to be muuuccchhh better and those are just much harder to find.People are still making it work in real estate though, primarily by getting more creative and often needing to add even more value to make the numbers work.

I'm trying to understand if the lease begins on the day of closing or the day after, if closing is at 2pm. 

Just got off the phone with another DIY landlord looking to hire a PMC.They really didn't like our response to their question, "How long does it take you to find a tenant?"

That quote will be the basis for any additional damage request. 

How much would you spend today for a monthly cash flow of $40k?

You’re going to have to buy at least $1M (or whatever you clear after selling costs.), worth of replacement properties, not $500k.

Those words from your CPA could ruin your day - or become your secret weapon.