Eventually, it got to the point where I reduced her role to part time and then had to let her go.

If you move forward with the LLC then reduce exposure.  

It had been appraised before listing at $378,000, listed at that price then reduced to $340,000. 

I plan to live in the home for at least 2 years to get the tax benefits but possibly longer, then possibly do a cash out refinance to invest in another property.Scenario 1: Current Rent- $3000/month Scenario 2: House Hack and rent out spare bedroom- If I rent out a 2nd bedroom, I'd still likely pay around $2600-3200/month on mortgage, taxes, HOA, CapEx & Maintenance (est. 8-10% depending on age of bldg)- The properties likely would break even around Year 5 or 6, so I may lose money each month if If I decide to move out before Year 5 or 6All of the advice I've read on house hacking was it's a good strategy to use if you can reduce your living expenses but a lot of the homes in Brooklyn mean I'd be paying about the same or more on rent each month.

So I wanted to be proactive and resecure all sheetrock on ceilings.

However, if you transfer the property to an S-Corp, you could potentially benefit from a step-up in basis while still qualifying for the Section 121 exclusion, though you would still owe depreciation recapture tax.If maximizing tax benefits is your goal, consider the following options:Selling before 2026 to claim the $250K/$500K exclusion while reducing taxable gains.Selling to an S-Corp to get a step-up in basis and claim the 121 exclusion, though depreciation recapture still applies.Keeping it as a rental and using cost segregation for depreciation but knowing that selling later will trigger recapture and capital gains taxes.1031 exchanging the rental property to defer taxes if you plan to reinvest in another investment property.Transferring to an SMLLC offers no tax benefit—only potential legal protection.

An LLC shields personal assets from business liabilities, while S-Corp taxation allows you to reduce self-employment taxes by taking a reasonable salary and distributing remaining profits as distributions, which aren’t subject to payroll taxes.

Not fully versed in every nuance of buyer/seller/agent negotiations, but as a future seller I hope to reduce my commission payouts.Cheers

Install landscaping that super low maintenance and reduces water usage and looks nice.

While Stessa is great for cash flow tracking and NOI insights, it lacks the structured accounting needed for tax reporting, loan applications, and long-term financial accuracy.If you're scaling and have multiple properties and business entities, double-entry accounting ensures every transaction has an offset, reducing errors and making tax prep smoother.