I always saw Detroit as a (dangerous) bet, but sometimes "le pegas el palo al gato" and sometimes you don´t.

It slows down the timeline, mitigates your risk, and let's you take your first ride with some training wheels. 

I’m currently structuring a two-unit short-term rental arbitrage opportunity in Seattle built around event-driven and seasonal demand cycles and would love feedback from others who’ve operated STR arbitrage or navigated major event markets.High-level structure:• Unit 1: May 2026 – January 2027• Unit 2: September 2026 – May 2027This staggered approach allows capture of late-summer tourism, fall sports, holiday travel, and spring demand, while also positioning around anticipated lodging compression related to the 2026 FIFA World Cup, which is expected to shift travel patterns before and after the event due to pricing and inventory pressure.The strategy centers on:• Strong operational leverage during peak periods• Risk mitigation through fixed costs• Demand diversification across tourism + business + events• Seasonal + event-driven ADR optimization• Hybrid short-term + mid-term stay targeting• OTA + direct booking channel diversification• Conservative underwriting assumptionsI’m especially interested in insights from anyone who has:- Operated arbitrage in major event-driven markets- Managed staggered lease timing across multiple units- Underwritten STR performance around World Cup, Olympics, or similar eventsHappy to compare notes or walk through assumptions privately with anyone interested.Appreciate any feedback or perspectives.

I’m currently structuring a two-unit short-term rental arbitrage opportunity in Seattle built around event-driven and seasonal demand cycles and would love feedback from others who’ve operated STR arbitrage or navigated major event markets.High-level structure:• Unit 1: May 2026 – January 2027• Unit 2: September 2026 – May 2027This staggered approach allows capture of late-summer tourism, fall sports, holiday travel, and spring demand, while also positioning around anticipated lodging compression related to the 2026 FIFA World Cup, which is expected to shift travel patterns before and after the event due to pricing and inventory pressure.The strategy centers on:• Strong operational leverage during peak periods• Risk mitigation through fixed costs• Demand diversification across tourism + business + events• Seasonal + event-driven ADR optimization• Hybrid short-term + mid-term stay targeting• OTA + direct booking channel diversification• Conservative underwriting assumptionsI’m especially interested in insights from anyone who has:Operated arbitrage in major event-driven marketsManaged staggered lease timing across multiple unitsUnderwritten STR performance around World Cup, Olympics, or similar eventsHappy to compare notes or walk through assumptions privately with anyone interested.

The first goal when underwriting is to mitigate downside risk on the deal.

I’d just price it right, maybe add some simple sound mitigation, and you’ll likely see steady occupancy.

It doesn’t handle maintenance coordination, lease enforcement, renewals, rent strategy, or risk mitigation.

I would say that this line of work we are constantly putting our lives in danger.

There are three ways to mitigate the taxes on flipping homes1) Expensive the overhead costs of running a flipping business2) Reducing taxable income of a small business through retirement account plans, Health Insurance payments, etc3) Entity classification - have a discussion if a Corporate entity will be helpful to you to mitigate self-employment taxes.Best of luck!

I always say that "Buying property at Tax Sales is the most dangerous way to buy real estate."