Need Pointed in the Right Direction Who to Talk To

[Jim W.]

Hey everyone, this is my first post on BiggerPockets - I've been a lurker for a couple months now!  :-)

I have a rental house that I've owned since 2003.  It's not a cash flow property right now... we probably make $50-$100/month on a quiet month (before accounting for any repairs or setting aside for things like a new roof).  Live and learn, but it will be paid off in 8 years, so it should be some good income at that time.

We just purchased a duplex a couple months ago to rent out both sides.  This one will be a nice cash flow property (see, I'm learning!).

I do have a property management company handle most everything for both properties.

Here's where I need some help with.  Up until now, I've always done my own taxes and it wasn't that big of a deal.  However, with this duplex (and I'm hoping to get a couple more in the next couple of years), it's starting to get a little more complex.

I'm sure I could just enter everything in and be good to go, but I'm concerned that I'm missing out on ways I should be structuring or handling things. For instance, there's the dreaded "should I put my properties under an LLC" question and if I go that route, is it better to have just one person under it or add your spouse as well. What I'm looking at though is more from the tax-advantage strategies vs the liability side. Other things like repairs - are there some strategies on doing things methodically to decrease taxes?

I know that I need to sit down and discuss this stuff with somebody, but I'm just not sure how to go about it.  I was thinking I should take my taxes to someone, but I've never done that before.  Do they sit down with you to discuss strategies or is that something outside of the scope of them doing your taxes?  Or do you talk to someone completely different to get guidance on this?

If anyone has any thoughts, please let me know - definitely appreciated!!

Thanks,

-- Jim