As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

Appreciation-focused investments can definitely help you grow your portfolio faster through equity gains, but they also come with higher market risks and usually require a strong exit strategy.

Joining BiggerPockets is a fantastic first step – it’s where so many great real estate journeys start.

To minimize upfront costs, explore down payment assistance programs, creative financing strategies like seller financing, or rent-to-own agreements. 

@Simon HorowitzNavigating the New York real estate market can be challenging, but with a focused strategy and strong networking, you can make significant progress.

@Tanner Davis If you want to pursue either a fix/flip or BRRRR strategy, it sounds like you might need to find a partner/investor that knows you well and believes enough in you as a person to invest money in a project. 

To say I am shocked is an understatement.Finally, when I sought out their tax strategy services, I specifically asked in the informational meeting if I wasn't acting a little prematurely, and if I should wait for my partner and I to be married in 2024 before making this investment, i.e. if tax strategizing would pay for itself in 2023 via significant tax refunds.

As for Cash flow, I think it depends on the deal structure as you mentioned, but also strategy/approach (cash flow vs building asset, holding long term).

Looking for any input or advice on how this strategy actually works.

Nightly rates: Yes, but the benchmarks should also be lower.Year 2 turnaround: What strategies could we implement to project a higher ROI in our second year?