I am in the parking sector, and simply put, as long as there is a deficit in parking in the area it should be a no brainer! 

We are wondering if it would be better to just off-load the property now at a ~85K loss, or hold onto the property while accruing large annual deficits in hopes that the property will appreciate back to our purchase price in the future.

That's because it doesn't take many years of strong rent growth to overcome the initial deficit, and then in each future year you continue to outperform.This strategy often appeals to investors with very long investment horizons.

As far as the argument for taxes being historically low and paying now vs later when they could be higher is very valid, however if you want to play the what if game, do you think there could be a point where the govt takes away the tax free status of roth accounts due to the deficit or social security that's run out of funding?

Unfortunately thats going to be yet another contributor to how ridiculous the deficit is going to grow over the next few years.Its funny how these same politicians were so up in arms but a few years ago about how critical it was to get the deficit under control.

Talk to a real estate lawyer about deficit capital restoration obligation to see if that is what you are looking for.

The appreciation factor is a fact, rents raising is as certain as the sun rising in the east, there is a more then 6 million unit deficit, that's not going to change or evaporate any time soon. 

Hospitals have not been paid for all the covid stuff yet, running at deficits. 

The hospital near us actually fired a ton of staff early on in COVID, and they've been hiring huge droves of travel nurses now to make up the deficit.  

This means you can’t qualify using the full rent amount you are charging and now have a deficit against your qualifying numbers.