Should i prepare a 1099 now if i paid more than $600 for work on the property but did not yet fill out a 1099 by January 31st?

You can but you need to upgrade to the online Self Employed version.  If you are using the Online Self Employed version or Desktop Home & Business program or Business program you can use Turbo Tax.

For Online Self Employed version,

Log into your account

Scroll down to Your Account and click on Show

Click on Create W-2s and 1099s

In your return, Anywhere on any screen you see....

Help me prepare and file W-2s and 1099s

Click on it and the side box will open, Then click on Quick Employer Forms in the side box.

Or from the Account Screen it will take you directly to Quick Employer Forms

How to create W2s and 1099

https://ttlc.intuit.com/community/forms/help/how-do-i-create-w-2-and-1099-forms-in-turbotax/00/25869

you do not give out 1099s to contractors unless they are engaged by your business.

If you send a 1099 now you will have a very unhappy contractor.

@gnagy