When Should You File?

Filing jointly just makes this messy.

If you make an estimated tax payment after the deadline, you can still get charged a small penalty, even if you end up paying more than enough for the year.

Since filing separate tax returns could increase your taxes, a "post nuptial agreement" would allow you to still file jointly but distinguish the properties for your other situation.

It can feel like babysitting half the time — constant check-ins, reminders, and making sure the right subs show up on the right day.What’s helped is building out real systems: clear scopes of work, milestone deadlines tied to payments, and weekly site walks.

.- Despite constant delays, missed deadlines, and refusing help (like us pre-ordering materials), we still paid him $12,000 (excluding PayPal fees we had to cover because of his lack of a payment setup).- He also let his worker sleep overnight at our property without asking.- We had to reschedule our lead inspection 3 times and missed our Section 8 window (cannot find another appointment for at least 4 weeks now), which directly cost us weeks of rent and more stress.- At the final walkthrough, he agreed to send receipts for his claimed overages before we’d consider any further payments.- Instead of doing that, he’s now threatening to take us to court over $200, saying we’re “mercenary out-of-state investors” and that the court will side with his “humble workers” who will testify on his behalf.- Still no receipts.

Still, the company has not acknowledged it or refunded me.My refund request (filed 7/1/25) was ignored until I escalated, giving them a deadline to respond by 7/11/25.

Hitting deadlines consistently builds massive trust and respect.3.

Yes, you should file asap or you really have nothing (anyone can file before you) - Cure!!! 

I was not involved in terms that were offered but expertise and ability to close on time and meet deadlines was all I could ask for.