At what point is it affordable? (bringing in the pro's when you have one property)

[Ryan McKay]

Hey folks, long-time/first-time!

I'm fairly new to "the game" with one property in Murphy, NC and not quite 4 months of operations under my belt.

Tax season is coming up and - as a newbie who is not yet cash-flowing (we went live right as the "slow-season" kicked-in, so while we have kept the weekends consistently booked by keeping our pricing relatively low as we build up some positive reviews, we're not quite covering our monthlies just yet and likely won't until the season kicks up in April.

Back to tax season though...

At what point does it make sense to start paying for professional help on things like tax planning, tax-prep, general financial planning, and the like?  Can you justify it with just one 2bed/2bath in your portfolio?

What sorts of budgets would you even be looking at? 

While our goal is - of course- to continue growing our portfolio with additional STR/MTR/LTR properties, I want to make sure that we are a.) at least cashflowing on the current property with a clearly defined horizon for profit before we add further properties, and b.) that we are neither jumping the gun on "buying" help we aren't ready for yet OR waiting to long and losing dollars in an attempt to save cents.

Guessing some of you have already been here and I would love any insights you might be willing to share!

[Becca F.]

@Ryan McKay

Congratulations on your first investment property! I've done my own taxes with TurboTax Premier with 2 rentals. I keep careful records of my income and expenses. I have a TurboTax CPA review my returns before filing. This year will be different since I did a major renovation on property #3 so I'll see how that goes once I start on my taxes. 

I think it's valuable to learn how to do your taxes on your own so you see all your numbers but it does take lots of time. Eventually I'll hire a CPA once I get tired of doing my own taxes. I don't have an LLC or S-Corp (for now). If I had an LLC I would definitely have a CPA do my taxes.