I've gone the single provider route and lost everything when she had medical issues.

If you can Househack a larger property, preferably one in a very good location for either business or vacation travelers, and one that is updated/can be updated I would suggest the airbnb route.

I agree with @Nathan G. using a real estate agent will be the best route as they already have the purchase agreements with all the standard contingency's built in.

Before you go this route, make sure that this truck does qualify as a 100% business vehicle, as opposed to a mixed business/personal use vehicle.

There’s a pedestrian friendly street on my block that naturally gets a lot of dog traffic, and every dog along that route barks at every dog passing by . . . . 

If I'm correct about that, then single fam may be a better route than small multi fam for Don... 

Change any of the factors in my example or add something I did not mention, and the answer might change, as well.And even if it does save you taxes in the current year, it may or may not be a good route to take, depending on other factors, including your intentions with this property and cost/benefit analysis.

If you go the self-managing route (highly recommended to save 25-40% of gross revenues), below are important points to know about self-managing STRs:Research local regulations to figure out what you need to do to have a legal STRResearch properties near yours on Rabbu or Airbnb to figure out what amenities sell and what you can add to stand outHire a professional photographerImplement a pricing tool like Wheelhouse, Pricelabs, or Beyond Pricing.

@Kyle Jones the traditional routes, or "conventional" routes, are the ways that we want to go.

I have not delved into the Wholesaling game as of yet, but see it is a viable route to earn my first paycheck in the real estate world.