This wasn’t a required expense.Property Taxes - $926.88We put in the offer to pay the full years property taxes vs. split them at the time of the sale.

You may be required to make estimated tax payments when the property sells.It depends on what your 2024 total taxes due were and 2025 estimated total taxes / withholding / estimated payments are.If you pay in atleast 90% of the current year tax or 100% / 110%(Depending on 2024 income), you are normally considered good.You may want to consult with an accountant for more clarification.

Are there any loans out there that require less than 10% down?

@Sujiro Seita Appfolio requires at least 50 doors

Obviously each deal is unique and requires proper due diligence. 

A STR is a completely different animal in my opinion, in that it requires more work and much more compromise, but financially is worth the effort. 

@Ken Almira don't buy a Florida condo w/o checking that they've passed their engineering inspection and their reserves meet the new requirements.

Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

How does their "generous liability insurance and requiring renters insurance" specifically benefit owners?

Being able to use real estate to offset taxable income requires some sort of participation on his end.If he wants you to be the boots on the ground, it will likely be hard for him to reduce his taxable income.