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?

[Jason Scavilla]

So my thoughts are like this…you can think of it like this. Her dog business has nothing to do with your finances. Find a house that will work for you and her business BUT do not count on her business making any money or helping with finances. IF it does then great but don’t plan on it and then this way you don’t even have to count on it. This can work for both of you, it can but the numbers have to work for you. I personally after being involved with real estate and having 3 rentals see that this for sure can work. I can see where you are hesitant, I was as well with my first but you can’t “calm you nerves” until you make your first purchase. OR you can have her “pay her share” and then there will be the potential that she can’t/won’t make her payment every month. Stress between both of you for this, her having to pay her share therefore  less money for her business to grow, potentially leading to her business not making it therefore leading her not making her monthly payments to you/the mortgage and you then losing the property. Yes that was a lot but to me that’s where I think.