Finally planning to get QuickBooks after struggling with manual 1099 counting for 20 years… Can it automatically add up my 1099s? Also, which QuickBooks version should I choose?

Hi everyone!

I’ve been manually counting the 1099s for my independent contractors every year and it’s been such a headache. I’m tired of spending days on it, making sure all numbers are correct. I heard QuickBooks could connect to Bank of America and automatically add up my expenses, so I want to know if that’s true.

If it works, what version of QuickBooks should I go for? I have a small real estate brokerage and I need a way to track everything easily.

Any help would be great, thanks!

QuickBooks isn’t available for download unless you’re willing to spend a lot. They only offer Enterprise now and it’s pretty expensive.

If you already have the data, I’d suggest using a service like efilemyforms. It’s super easy to upload everything, and they handle all the filings.

@Hadden
I’m okay with paying for whatever will save me time.

The stress of manual counting every year is getting to me. I just need something that connects to my Bank of America and automatically sorts and totals all my expenses. Do you think QuickBooks is worth it, even if it costs a lot?

@Cove
How do you currently keep track of your expenses? If you know what you’ve paid each contractor, using an online service is easy. How many contractors are you working with?

Hadden said:
@Cove
How do you currently keep track of your expenses? If you know what you’ve paid each contractor, using an online service is easy. How many contractors are you working with?

He isn’t keeping track.

@Shan
I figured as much.

Hadden said:
@Cove
How do you currently keep track of your expenses? If you know what you’ve paid each contractor, using an online service is easy. How many contractors are you working with?

I go through all my bank statements by hand at the end of the year.

I thought tracking every single transaction throughout the year would be too complicated, so I’ve just been doing it all at once. It’s become more difficult now that my business has grown, and the workload keeps increasing.

@Cove
That sounds rough. Have you thought about getting a bookkeeper? It’s not too expensive and could save you a lot of stress. A few hundred bucks a month could keep things up-to-date and save you time.

@Hadden
I know, it’s crazy I’ve been dealing with this for so long. But at this point, it’s just too much. I love working in real estate and putting in 100+ hours a week, but the tax stuff just crushes me. I enjoy other parts of my business like marketing, but the accounting side of things just isn’t for me.

I think hiring someone would be another expense I don’t need right now. I’d rather do it myself in a simpler way than spending days counting things manually.

I do track revenue and expenses on a calendar, but the 1099s and the manual work in April are my biggest pain points. Hopefully QuickBooks will save me from all of that.

If I can spend a full day setting up QuickBooks to do most of the work for me, I’d be happy. In the past, it’s taken me about a week to do everything, and I really don’t want to go through that again.

@Cove
You really need your accounting software to track income properly.

You shouldn’t rely solely on 1099s. You need to report all income, even if it’s not listed on a 1099.

Shan said:
You shouldn’t rely solely on 1099s. You need to report all income, even if it’s not listed on a 1099.

I get that, but the 1099s are step 1 for me. I have to send them to the contractors and to the IRS every year.

Then in April, I deal with the expenses.

Just to clarify, I’m the one paying the contractors, not receiving the 1099s.

@Cove
That clears things up. QuickBooks should help you issue the 1099s to your contractors.

Shan said:
@Cove
That clears things up. QuickBooks should help you issue the 1099s to your contractors.

Do you know if QuickBooks will automatically itemize all my expenses and contractors once it syncs with Bank of America? And which version of QuickBooks would be best for me to download?

Here are the options I see:

QuickBooks Desktop Pro
QuickBooks Desktop Premier
QuickBooks Desktop Accountant
QuickBooks Desktop Enterprise
QuickBooks Mac Desktop
QuickBooks Point of Sale

@Cove
No clue. But from what I know, QuickBooks isn’t great.

@Cove
What you need is QuickBooks Enterprise 2024. You can get a license from a trusted reseller.

You could export your bank transactions to Excel, then sort and sum everything for the totals.