Having the reassurance that I’m not chasing my tail really helps. 

In fact, by my amateur eye, it seems houses improved by the tail end of WWII particularly with regard to foundation construction.

Do you think that since we are at the tail end of the pandemic (I hope) that the jobs being lost due to the Corona virus was a thing of the past (early and mid pandemic) are behind us?

@Travis FairbairnGoal will be to buy at a discount, so tax tail doesn't wag the dog

And will definately keep busting tail to get this going.

I'm referring to what I've read called "Whole tailing" which as I understand it, refers to buying a off-market property that does not meet your criteria as a long term hold and fixing it up just enough to flip.

On newly acquired properties in the Berwyn and Cicero markets where rents are $200-400 under market, I will probably do an aggressive rental raise once we are through the tail end of the Covid era.

Do not let the tax tail wag the business dog.In your first example, it will be taxed at your ordinary tax rate.

I see this all of the time- someone works their tail off to find an off market deal and it falls apart during escrow because there are two inexperienced parties trying to make it happen and they don't know the process. 

It was as if they had zero understanding that they wouldn't return back to their home in spite of being served with the paperwork by the court and then the sheriff's deputy.We worked our tails off to get a full house out onto the lawn.