There are some valuable insights here regarding property purchasing, though unfortunately, house-hacking doesn't seem feasible in this scenario. Initially, I would have recommended starting out in the short-term rental (STR) space through house-hacking. The concept of purchasing a multi-family property, utilizing one unit for STR, and eventually transitioning the entire property into an STR setup after a year is quite appealing.
My journey began with properties I owned, where I dove into the STR industry. Upon separating from the military, capital became a constraint. However, drawing from my success with two STR properties, I ventured into "Arbitrage" to leverage my expertise. Surprisingly, this decision has led to building an Arbitrage business generating much more cash flow than I had imagined. I am now back to purchasing properties.
I want to be clear "arbitrage" is NOT investing, but running a hospitality business. Renting properties for STR does not come with the upsides of tax savings, appreciation, equity build up, etc.
I agree with the sentiment expressed by others that diving straight into STR, especially with a property that is cashflow negative as a long-term rental (LTR) or through arbitrage, can pose risks. Nevertheless, as with any venture, risks can be mitigated with knowledge. While the STR market is undeniably competitive, it's not saturated. Success hinges on one's ability to craft exceptional guest experiences, market properties, and implement systems for cleanliness and customer service.
Despite the skepticism surrounding "course gurus," I would suggest considering a reputable course, particularly if pursuing the arbitrage route. Investing a few thousand dollars can provide a comprehensive roadmap and access to a supportive community of like-minded individuals. Although I haven't personally enrolled in such a course, a single free webinar bridged crucial gaps for me to kickstart my business in the "arbitrage" route.
For those inclined towards purchasing STR, I recommend exploring the offerings of the Short Term Shop. Their podcast and book have been instrumental in shaping my knowledge base. Their brokerage specializes in guiding individuals through the intricacies of STR investments, providing invaluable support and training.
