However, at the start of 2020, records have been updated, as it now shows one owing $9000 and the other owing more than $11000 (turns out that other liens can be ultimately attached to property taxes if not paid in time—in this case the county wants to recoup expenses incurred in nuisance abatement and demolition).

The house is generally in very good condition mechanically (newer boiler and on demand hot water heater, PEX supply plumbing, new outlets, switches, light fixtures, updated electrical panel with breakers, fresh flooring, fresh paint, etc).

The property needs new windows, some kitchen and bath updates etc. 

It is in good shape, but really needs an update (last remodel was early 80s).This is Hendersonville, TN, and the market is hot right now, especially in our neighborhood.I’m looking for advice on how to tip the odds in my favor.

Once updated, you could also do the Airbnb thing in the meantime. 

At the end of the day, in my opinion, I would keep them updated even if they don't invest in the deal so they can build a stronger trust level with you.

During the sale process and while i was also purchasing insurance for the condo, i reached out to the HOA company to ask when was the roof of the condo was last updated.

Don't forget to update your insurance when / if you use an LLC to hold the property.

UPDATE!

@Kimberly Kesterke Any updates today Kimberly?