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

I am also a huge fan of real estate and for the past 50 years there's been a way to combine both.By leveraging a Self-Directed IRA, real estate investors enjoy both the traditional advantages of property ownership and the additional tax benefits of retirement accounts, creating a powerful wealth-building strategy.

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

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.).  

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?

Then plan and design how you're going to deploy that cash via what strategy your wife and you have confidence in.I use a excel or google doc and my first sheet would layout all of the details of the sale including all costs that go into getting closed.

Here are a few strategies to consider for funding a down payment:Partnering: Like Gregory mentioned, finding a partner who can contribute to the down payment in exchange for equity or a profit share is a solid option.HELOC or Cash-Out Refi: If you have equity in your home or another property, a home equity line of credit (HELOC) or cash-out refinance can provide the funds you need.Private Money: Reach out to friends, family, or private investors who may be interested in lending you the down payment with a promissory note.Seller Second: In some cases, the seller might agree to finance a portion of the down payment as a second mortgage.Live Frugally and Save: It takes time, but reducing expenses and setting aside funds from your income is a tried-and-true method.The right approach depends on your situation and deal structure, but a mix of creativity and resourcefulness can go a long way.

As I approach my move out strategy where I will be converting my upper unit into a STR, I often think of guest interaction amongst the two units.

This is going to vary widely depending on the strategy and real estate asset class.

Leveraging equity does involve some risk, so it's important to have a sound strategy to avoid overextending yourself.