Property going down hill fast! Advising friend-Denver. Keep, fix, sell OR sell @loss?

[Tanya Solomon]

I'm hoping someone will have a good idea(s) on how to damage control a worst-case scenario. This is like the Kenny Rodgers song "You gotta to know when hold them, know when to fold them, know when to walk away and know when to run." 

Does anyone know a GREAT financial advisor (who has a strong background in RE) who can be hired to help figure out major $ life decisions/strategies? Especially someone who is well-versed in dealing with ppl who are in decline but are not entirely ready or willing to be open-minded about new strategies or ways of living. Strong, brilliant, dynamic, hard-working/dedicated types great mid-life (where would our world be without them?) but CHALLENGING to raise as children and then difficult in the "twilight years" bc they can't do what they used to and have a hard time accepting this.  

TLDR: This is a "pick your poison" situation. The 1st "macro" question is -In general and this market/time of year, is it better to fix a home's essential/habitability issues before selling or just cut the losses?*

Is it better to fix problems that are essential/determine habitability and hold/wait to sell the property when the market is most favorable to sellers to sell

or

To cut the losses, get out while you can, bc it is not financially wise to spend months/yrs of your time and hard-earned $ if you end up turning around and selling it right after the repairs are made. There is a fairly good chance that coming out even would be the best-case scenario. 

I FULLY UNDERSTAND THAT NO ONE HAS A CRYSTAL BALL AND CAN KNOW WHAT CAN OR WILL HAPPEN IN THE FUTURE. This is an IN GENERAL question

*The rough math/facts:

-Home is in North East CO (just outside Denver)

-Home has been used primarily as a STR and has years of earnings around 50k per yr. It is now occupied by my friend.

-latest comps support about 450K if the home had no major issues. This is WITHOUT taking the issues into the equation what the home could sell for "on a good day"

-Cold calling to get est. They are coming back at around 100k total to fix the foundation and replace/repair the roof. The work itself will take months due to seasonal issues and how far out local foundation repair companies are booking out now. We have been unable to find an "emergency foundation repair" or a way to stop the slow ruin of the home due to the significant foundation issue(s). 

-The home is owned outright (no mortgage) and my friend is single, middle-aged, and has no children. Elderly mother can help with $ but is not rich herself and obvi taking retirement $ from one's parents is a worst-case scenario.

-Friend has been in an accident and has been experiencing significant health issues with no end in sight and has NO INCOME. The health issues have been so significant that my friend has taken the 3 properties owned off the STR market. Chipping away every month from a little $ nest egg. This is not a sustainable model and $ will run out by the end of 2024.

We have asked ourselves "Can it get any worse?" Only to find out that YES it can indeed get worse. Unfortunately, I live 2000 miles away and have a family/spouse + school-aged kids. I do not have the time to fly there and stay for weeks to get things taken care of. 

It is so hard to watch my good friend not only have to deal with significant health problems alone but see how they have gone from a dynamic, resilient, wicked smart person managing 5 properties AND holding down a 30-40 hour a week full-time job to sustaining an accident and having their life fall apart like a slow-motion train wreck. 2 of the properties in their portfolio had to be sold just to get $ to live off of. 

My advice has been to sell all the properties, get back as much of their health as possible and then look at how to invest what's left. What I don't want to see is the throwing of good $ after bad AND the upside of selling at a loss now is that we will know what the loss is and can start the "rebuilding" immediately or whenever they feel up to it. My friend feels like they are losing so much and have invested so much time and $ into the home and properties left, that it is too hard to think about selling. It feels scary and they are worried that the $ will just quickly run out and they will have nothing left. My friend is essentially holding out for a miracle to happen and for these problems to go away and or address/acknowledge head-on that they will probably never be like their former self. I can def see how that is a difficult pill to swallow.

I came here to find ppl with experience in not only real estate but also with the careful balance that one must achieve and then keep wealth. Maybe someone recently helped/advised an aging family member on the best way to  set up their lives to be on "auto-pilot" 

Do you have ANY recommendations?