IQuestion knows taxes, maybe she'll weigh in on some of your post when she sees it. I'm not sure about your 40 something friend, as far as what he can legally do----I certainly don't know about stopping house payments then getting retirement early if he's still making $$ somewhere. If he's making tons it would be hard to do this balancing act----sounds like he needs to pay his house off with his tons first. I wouldn't know how much that 'ton of money' is that he makes. Those who really have lots of $$$ indeed can do certain things to their personal & biz tax advantage. They retire when they want, also use accountants to advise such so that Mr IRS doesn't come knocking.
I saw that MS text posted here about the med building.... you're right, didn't have income for a $9 mil investment AND no lender would have been able to justify loaning them that either. GEEEEZ, like was MS trying to impress that potential buyer with the fact that their (daily interest $1016.10) monthly payment is $60,197.75????? Anyone here know if that's correct? I'm checking the Bates to be sure not a typO. Ok, that's apprx $723,000 a year just for med building payments---after paying that, employees have to be paid, office supplies (gotta reimburse SH for some of that), Sievers own house payments, student loans, personal living expenses like food-clothing-car maintenance-kids med care, lawn care, pool maintenance (didn't they have that?), Marks' Whole Foods runs, not to mention vacas here & there, hotel stays in Naples. Oh, I left out the gf who needed Attny fees paid (but there was a reimbursement) AND burner phones. NOW I have no idea how big that entire med building is, when it was built, or what it's worth----but I can't imagine Sievers' 5 units in that med building would be worth $9.75 mil at time of their hopeful sale back then. UNLESS he had lofty hopes of selling for that? That would be $1.95 mil per unit.
Forgive me if I'm way off here.