Lots of wooden features to the interior so possibly explore updating the kitchen cabinets or the living room bar set with a fresh coat of paint?

Sending contractors in before anything is under contract sounds like it will rack up tons extra cost (presumably you're paying the contractor for these bids on homes you dont even own?)

Life was good… until covid hit and some various health conditions left me out of work, depleting saving and racking up debt.

. :) I would use the old John Wooden "Be quick but don't hurry" as you expose yourself to the process.  

We purchased the house in winter and we built wooden steps to make it safe/operable and because the weather wouldn't allow us to do masonry right now.

This would prevent guests from using the jeep for any reason other than going up and down the driveway, prevent damage caused by the chains at high speeds, and prevent me from having to explain to guests how to put the chains on the jeep. [2] Until I can afford to pave the driveway, build classic-looking wooden guard rails to guide up the mountain.

Also if the flooring is a wooden floor is decent condition would you get LVP or just keep the floors as is ?

They take great care of the house BUT, recently racked up an HOA fine after 4 repeat warnings from the HOA, and today I find out there is an outstanding utility bill from when they moved in April 2016 that they have not paid in the amount of $600.

Wish it had occurred to me to start when I was in college before I racked up student loan debt.

If someone can rack up 19k in back taxes without being foreclosed on by the state, I would worry broadly about the eviction laws.