However, a caveat is that we will accrue these losses across the entire year; they don't exist yet.My understanding is that IRS safe harbor laws could allow us to simply pay 110% of 2025 taxes (or 90% of 2026 taxes, however this will be hard to predict ahead of time).

🤔[Obviously, IRS is not going to chase a $25,000 tax debt beyond the ten years.  

These are instances where landlords should weigh these factors in determining whether to evict or work with the tenant.

Since the home was moved into an LLC and taxed as an S-Corp/Partnership, it’s technically no longer owned personally, so the IRS usually won’t allow the Section 121 exclusion.

You asked about short-term rental property demand and mid-term rental property demand in other areas besides yours and thoughts on managing these properties.First off, short-term rentals are a great property class to own, especially if you "materially participate" with 500 ours in the management of your property for the IRS to consider it an active investment and able to write down your active or W-2 income with the expenses, bonus depreciation, and cost segregating the property for additional depreciation to reduce your income taxes.There is short-term rental demand in many communities in Michigan because we have so much coastline and natural beauty as well as university, business, and hospital stay demand.

I want to make sure our record keeping, bookkeeping, and ongoing W2 withholdings are all fully IRS-compliant from day 1.-- Bring another expert onto my team, who can help maximize the overall strategy.Now, how much to spend and for what services ...Why am I posting these? 

From the IRS Profit motive safe harborAn activity is generally presumed to be for profit if it has made a profit in at least three of the last five tax years.

Also: many - but not all - liens are renewed by the IRS before their 10-yr expiration

From a tax perspective, the IRS typically allows pre-rental work (like the hours you spent getting the property ready) to count toward material participation if it’s directly related to getting the property ready for rent.

Hi @Linda Cunliffe, If you sell to a relative below market, the IRS treats the discount as a gift, not a deductible loss.