Granted those units are in really good condition, but Won’t be as updated as the ones we are working in now, even still, I think that their current rent is far below the going market rate.

On the other hand, it's apparent in the county minutes that they're at a loss for what to do with the property or who would potentially want it given current condition and zoning.Does anyone have stories, tip, or tricks for buying properties from their county's "delinquent tax list," before they go to auction?

If someone tells you they are struggling, have a list of resources handy where they can reach out including mental health hotlines.

The HOA is well-funded, everything on the property has been recently renewed (roofs, roads, pools, gardening, etc).I am curious as to whether market conditions are shifting because of local short-term stay bans (which might have opened up a lot of housing stock), COVID, over-building, or any other factors.In a town of 20k people, apartments.com lists around 3800 available rental units.

I’ve taken conventional routes so far, so maybe the conditions allow for creative options.

I feel there is a bunch of risk with this and really just want to get it off my hands as cleanly as possible.I have a relative who owns a house free & clear 4br / 2.5ba house that is around ~250K fixed up but is currently in bad condition.  

@Edward R.If you purchase a property and it is vacant and there it is not in livable condition - you may not get the tax benefits that you are looking to achieve.

On October 6th, 2020 after a long time not working and battling health issues I decided to brush myself off and get back in the game.

You've got a good path forward planned out here.The one mindset thing I want to encourage you to tweak here is about the price/value of the home -- I see people making this assessment every day and it monolithic and rarely ever as simple as:  the home has been on the market longer than the average Days on Market so somethings wrong (price, terms, or condition).It MIGHT be true, but there are a dozen other things that might be true. 

There's an argument to be made for a sliding scale depending on the age of the home and the condition of the systems.