They’re assuming eventually the timing will line up.In real estate, with the amount of data we have, we can be more intentional about that.

Eventually you may want property management. 

If the average stay is 7 days or less (or 30 with significant services), that unit can be treated as non-passive if you materially participate.In your case, only one of the four units is an STR, so it doesn’t automatically convert the whole property.

A LTR in order to cover the bills then convert once the construction is over.

That’s the scenario I’m trying to avoid.I’m finding that the hardest calls are the ones where the deal pencils if the signals eventually converge, but you’re still in that fuzzy middle zone.

I prefer not to have two properties for sale at the same time because carrying the mortgages on both properties would be financially burdensome.My questions are:Can I provide a two-month notice by January 15, with the lease converting to month-to-month after the annual lease expires on February 15, 2026?

Just because mortgage rates have dropped significantly and values ill eventually peak in 18-36 months in this market.You can fix & flip and then 1031 echange if not your taking that Captial gain hit. 

But I know you could go without a property management software like Hospitable for example and work directly on the listing platforms but it eventually comes down to dollar cost vs time cost.

I’m a practicing physician who recently started learning real estate more intentionally after relying mostly on traditional investing.My goal is to replace step away from call in ~ 10 years (or sooner) and eventually replace my income in 10-15 years.

Since you would have converted the property to investment, you could also do a 1031 exchange, which allows you to defer all of the tax and reinvest it in other investment proeprty/properties.