Yes. When you sell depreciable property you must recapture all allowable depreciation. So even if you don't take all allowable depreciation the IRS will treat the sale as if you did take all allowable depreciation which is what is subject to recapture. Recapture is at a lower rate than you initially took the depreciation, plus it's in unknown future dollars that are worth less than today's dollars.
The thing that is difficult for many people to understand is that the benefits of accelerated depreciation are in the time value of money. The guiding principle is that a dollar today is worth more than that same dollar tomorrow (or any future date years down the road). This makes sense when you think about it. You could buy a lot more with $100 20 years ago than using that same $100 today. 20 years from now that same $100 today may only be worth $75 in future dollars.
Imagine the IRS says they're going to give you $100, but you must repay it at some unset point in the future. They give you two options on how to receive this money: over 5 years with accelerated treatment or over 27.5 years with straight line treatment. If you take it over 27.5 years you get $3.63 per year for 27.5 years. If you take it over 5 years you get $40 in the first year, $24 in the second year, $14.40 in the third year and $10.80 in the fourth and fifth years.
The idea is that the sooner you receive this money the sooner you can reinvest it into something that will produce a return instead of just letting it sit there in the US Treasury waiting to get it little by little and reinvesting the small portions each year.
So just looking at it year by year shows an obvious windfall in cash flow over the first 5 years, but the key is to make the money work for you.
This is how it would look: For simplicity sake let's say you hold the cash for the first 5 years and then reinvest it. In the 5 year example you'd have $100 to invest after 5 years. If you then put that $100 into something that compounds annually and has an 8% interest rate for 15 years you'll end up with $317.22 after 15 years of investment, 20 years since purchase. In the 27.5 year example you'd have $18.18 to invest after 5 years. If you put that into the same investment that compounds annually and has an 8% interest rate for 15 years plus you get to add another $3.63 to it every year you'll end up with $164.12 after 15 years of investment, 20 years since purchase.
So after 20 years you would either have to recapture $100 with $317.22 available or recapture $72.72 with $164.12 available. Now the thing here is that recapture maxes out at 25% while the actual depreciation is dependent on your marginal tax rate. So in a "perfect" situation you're at the top marginal tax rate of 39.6% for the actual depreciation and recapture at 25%. In this situation your recapture is only 63.13% of the actual depreciation. So your true recapture would be $63.13 vs your $317.22 available or $254.09 surplus after recapture on the 5 year example; Or your recapture would be $45.90 vs your $164.12 available or $118.22 surplus after recapture on the 27.5 year example.
So there you have it. It absolutely makes more sense to accelerate depreciation whenever possible. The reality is they don't just give you $100. The $100 here is the entire building/improvement value and the rules for depreciation are quite complex. Out of that $100 there could be $10-$30 classified as 5 year assets, $10-$20 classified as 15 year assets and $50-$80 classified as 27.5 year assets based on the facts and circumstances of the property. Since every property is unique you need to have documentation to substantiate your depreciation. The only way to do this that is accepted and approved by the IRS is to have a qualified construction engineer or architect do a cost segregation study on the property.