First Property Advice Needed

[A.S. Minor]

I am on the path to purchasing my first home. Ultimately, I plan on "house jumping," for lack of a better term. I would like to buy my first home, and after a few years of living there, buy my second home, move into that one, and rent out the first. Then we rinse and repeat. I was looking for advice on whether this plan is advantageous in the long-term, or whether I should adjust it based on the factors below. The adjustment that I am considering is whether I should try for a duplex/triplex for the first home. This was my initial thought process, but (A) I was having difficulty finding them for sale in my area (Volusia County, Florida), and (B) the below information:

My girlfriend is a dog trainer, and her business goals involve board-and-trains, meaning we'd need enough space to house at least a few dogs for a few weeks. That's not the focal point of my investment, but it is a factor that must be taken into consideration. So we have to consider space, of course, as well as any zoning restrictions (she's been focusing on that aspect). But if we were to get a duplex, we would also have to factor in information regarding tenants (allergies, small children, etc). Now, when I do begin this journey, I've kept in mind that this first property is not our long-term home. Our second property is likely to be longer term. Ideally, I would like to continue this jumping until we've accumulated enough properties to pay for our final home, but depending on the circumstances I'm flexible when it comes to which one will actually be the one. 

Obviously there are more factors to consider when combining the idea of a multi family unit with this business plan that she has. So that's my ultimate question: Whether this plan seems feasible with a duplex/triplex, or whether I should just stick to single family homes. We're not looking to have an entire complex of dogs in this first property, but at least 3 or 4 for a few weeks at a time. What are your thoughts on being able to combine her goals with my own?