As a general rule I would always say it is better to get a return on your equity rather than leaving it sitting in a property you own free and clear.

Feel free to message me if you want to Network.

The majority of taxpayers are required to settle their tax dues by April 18 to avoid penalties and interest accruing on any outstanding amounts after this date.For those residing in Maine and Massachusetts, the deadline is extended to April 19 due to the Patriots' Day holiday in these states.How to Request an ExtensionIf you find yourself in need of an extension, the IRS provides convenient options to make the process smoother:File Form 4868:Utilize your tax professional, tax software, or the IRS Free File platform on IRS.gov to submit Form 4868.Individual taxpayers, regardless of income, can leverage Free File for an automatic extension request.Electronic Payment Method:Make an electronic payment using Direct Pay, Electronic Federal Tax Payment System, or debit/credit card or digital wallet.When selecting the payment type, indicate it's for an extension.

Yes if it is primary and you lived there for 5 years, probably do not need 1031 as up to 500k is tax free for married filing jointly and 250k for individuals.

If so, then it should be a tax free sale.

Feel free to message me if you want to chat further. 

Devang,  We had a free & clear property that was vacant we were considering for rent; In my area we estimated it would rent for roughly $1k per month.

This allows our buyers to purchase the property, make the necessary improvements, and then choose to either rent it at market rate or sell it.Selling a property without providing at least two exit strategies for the buyer significantly decreases our pool of buyers.Feel free to reach out, you could send me the numbers and I can give you my opinion on what would be a good deal to a buyer with keeping the tenants. 

Especially for STR, you could literally put a sofa bed in the living room and accommodate extra guests (before you all scream, this is fairly common even in high end STRs and I've never heard of complaints, but feel free to cite other experiences).

If you've got good skills on Insta and TikTok and can build a brand there, that's free, and then you can link directly to your site.