If the latter, how does that look on a day to day in terms of operating, marketing, and the ownership structure?

From both a real estate and STR perspective, the key to success will be choosing the right market first.

If you do not qualify, you would then look into if you would qualify with renting your departing residence. 75% of the lease will be used to offset that departing residence mortgage. as you mentioned the timing of renting the place can absolutely be tricky so you would hope you do not have to do this.Finally, and I guess would be sorta of a trick, but we do bridge loans on occasion in this case IF you can qualify once you get the property rented at market value even if debt to income ratio is too high before it is rented.

Are you looking into certain investment strategies to begin or certain markets? 

Guest breaking down their markets and strategies gave me a lot of insight.

Hiring the right GC is key to getting the property market-ready efficiently.

Focus on market research by exploring neighborhood rent trends and property values while considering your financing strategy (house hacking, BRRRR, or buy and hold).

Even if you get a great deal that is 20% below market, appraisers will typically be anchored by the last sale price and you may be stuck not being able to pull out as much cash as you need to pay off the HELOC.

Market Demand: Buyers love move-in-ready homes, and flips are often the most attractive properties on the market.

I'd be happy to visit about the market.