Should I stay or should I go now?

[Tasha Rivard]

This is my first ever post on BiggerPockets though I have been lurking for years. I’m intimidated to say the least 😂). I’m hoping this community could help guide me in the right direction! Here’s my situation: 

I currently own a home the vacation destination New Smyrna Beach, Florida. It’s a 3/2 pool home that’s not on the beach but close enough to be desirable (10min), but is only zoned for midterm rentals. I bought it in 2020 and have a 2% interest rate.

I’ve been casually looking for an investment property for a while and found a great deal on an ideal AirBnb house a town over in a similar neighborhood/distance to the beach/other attractions. This one IS zoned for short-term rental. Given the fact that I’m single and have zero dependents I figured it may make sense to move to the new house for at least a year to get a primary residence mortgage with a lower rate and rent out my existing house as a furnished mid-term rental.

My question is around taxes: my current home needs significant repairs and updates (about $20-30k’s worth 😬) before it’s ready to be rented (the pool enclosure went partially down during a storm among other things). I’m *thinking* that if I start renting my original property this year and move to the new house as a primary, those repairs can be deducted? What about any repairs I’ve made earlier this year? What if after 1 year in the new property I decide to move back? How should I legally structure all this?

For reference I work a full-time remote W2 job but I do have the time and bandwidth to do this. The numbers seem to check out, but there still a lot to consider that’s over my head… What would you do in my situation?

I’d also love to connect with a knowledgeable real estate CPA as well as a lawyer in the Orlando/New Smyrna area if anyone has recommendations! I’m super excited to get started in real estate to have access to this community!

TIA!