Don’t forget. Even if this works. You aren’t creating new deductions, you’re simply pulling them forward so you’ll have less deductions in the future. Every time you lower your tax bracket you are lowering the value of the deductions. So while deductions today are generally worth more than future deductions. That could be offset by having the deductions applied towards lower tax brackets.
Imagine you make $100k and you are affected by 3 tax brackets.
0-33k =-33K 0%
33,001-66k 10%
66,001 - 100k 20%
You can take $100k in deductions this year and pay zero taxes, for one year and then $10,100 for for 2 years ($20,200 total)
You can take 67k in deductions this year and pay zero taxes for a year, take 33k the second year and pay $6,800 year two and $10,100 year 3. ($16,900 total)
You can take 33k each year and pay $3,300 in taxes all 3 years. ($9,900 total)
Obviously this is simplified but unless you expect to make much less and be in a lower tax bracket in the future those deductions could come in handy. It’s pretty much a reversal of the Roth conversion strategy.
But as mentioned. I don’t think the tiny house would get you there. You’d have to convert your LTRs to STRs. I could easily see you spending more than you save if you try it with a tiny house.