The industry is mature and margins have properly compressed.

Plus, you’d probably reach your goals faster with that plan of attack if executed properly.

Transparency and professionalism are core to how we operate, and we ensure all properties have clear, insurable titles before closing.

Setting up direct bookings is a great way to save on fees, but you’re right—it requires extra effort to ensure everything runs smoothly.For vetting guests, start by asking a few questions when they inquire, like the purpose of their stay, how many people will be there, and if they’ve stayed in short-term rentals before.

From my experience working with over 400 investors, avoid transferring your home into an LLC (it can trigger loan issues), be mindful of capital gains taxes when selling, and ensure your debt-to-income ratio allows for your next purchase.

Also, ensure you're compliant with New York's security deposit laws, which cap deposits at one month's rent.

Consider defining clear roles, ownership percentages, and responsibilities upfront, and ensure you’re protected if the partnership doesn’t work out.Since you already own properties, it might be worth consulting a CPA who specializes in real estate for advice on tax strategies specific to your situation.

Sometimes, properties owned by non-profits have deed restrictions, zoning conditions, or agreements tied to their use.Tax Considerations: Non-profits often hold tax-exempt status, so you’ll need to ensure that taxes are assessed correctly once ownership transfers to you.Potential Public or Internal Scrutiny: If the transaction appears to undervalue the property or is perceived as exploiting a non-profit’s resources, it could lead to reputational risks for you or the organization.

I underestimated utilities in my early years, so I ensure those are properly captured (electricity, gas, water and trash).

In a worst case scenario like the house burns down or a tenant sues you and you're not insured properly, that's a big risk.