If you continue filing taxes jointly the income you realize from your separate property will still need to be explained and redacted, regardless of the type of entity holding the real estate.

Today, the injunction was struck down. Register your corporations by Jan 13, 2025

It worked out beautifully... they met their deadlines and profit goals and had the break they needed.Perhaps selling one property sooner is the solution?

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

Will there be any issue on Jan,15th deadline in this case ?  

It wasn’t an issue of “underwriting does review a file until it was complete”.

You might need to file 1099s if you used contractors or other people whom you paid for labor:https://www.biggerpockets.com/forums/51/topics/1167632-expla...

My only goal is to have all the details clearly spelled out so we can adjust price and deadlines in a fair manner as things come up. 

Quote from @Zara Massoud: Your new PM is correct and the old ones were wrong.The property manager must have your social security or tax ID number on file.

As far as your primary residence, if you have lived in it 2 out of the last 5 years, you should not have to pay taxes on capital gains (difference between what you paid for it & what you sold it for) up to $250,000 if you file your taxes as an individual and $500,000 if you file jointly with a spouse.Just a disclaimer, I am not a tax professional.