The property is at a good price ($925k for a West Town four flat that's been pretty run into the ground w/ no rent increase in 20 years) but all the other variables throw off our deal math.

At $2.3M with $850 average rents this looks like a nice property that is basically a bond, not a value add, so if the cash flow feels thin your math is probably right.

I've tried modeling out:Buy a 700k property w/ a mortgage (20% down).Use CostSeg / Bonus Depreciation to offset 37% tax bracket w-2 incomeOperate it (materially involvement) to a break even cash flow (including debt) for 1 full year.Sell it and 1031 into a 800k property.Repeat 3 times.Sell the final property (now at 25% bracket)Assuming appreciation covers "other costs" my math keeps saying this is not as valuable as just sticking the original 200k (140 downpayment plus other costs (legal, closing,etc)) into fund.I originally convinced myself the bonus dep was a no brainer, but now the math isn't working out.  

Talk about competition (more like not doing your homework)🙃  Beginning bid of 100% of the assessed value is game over for tax sales as far as I’m concerned.

Tax strategy changes the math dramatically.

───The price range that consistently wins:$100K–$150K* # Deals: 15 deals* Avg CoC: 7.5%* Avg Monthly CF: +$179/mo$150K–$200K* # Deals: 4 deals* Avg CoC: 2.5%* Avg Monthly CF: +$82/moThe $100K–$150K band is where the math works in this market.

VA assumables traded at 3-8% over list in 2023-2024 in competitive markets because that math was compelling.Your conventional loan is not assumable in the traditional sense, so you cannot sell the rate as a standalone asset.

And when buyers compare resale at 6.75% vs new construction at 3.99%, (with concessions), the math gets ugly.This is why many resale listings are sitting.It isn't condition; it isn't price; it IS financing leverage.Builders can manipulate the payment.Homeowners can’t.So while headlines say “home prices are holding”, the real story is that individual sellers are competing against corporate balance sheets.

The Math is Tight (The $3.5k Ceiling)This is the hardest pill to swallow.

As mentioned above your math for the spread may be missing a few items and somewhat thin.