Older people like this often need a little extra help with technology.

You can lower the price.The buyer can pay the extra $9k in cash, if they have it.The buyer can walk away with their earnest money and you can lower the price $9k for the next buyer or require them to bring $9k in cash. 

If you need a reliable roofing contact, let me know—I’d be happy to recommend someone.Your agent should have negotiated a clear possession date that accounts for the seller needing extra time to move.

If you buy an outdated smaller 2bd/1ba home for $150,000 in an area where remodeled 3bd/2ba homes are selling for $300,000, and you know it will cost $50,000 to update the home and add an extra bedroom and bathroom, you can be relatively sure you will be able to recoup your investment. 

It seems like another layer of things to keep up with, and I can't figure out what the benefit would be.

It does depend on a few things as you know like price, location, and the extra's like what's there like water. septic, electric etc.Do you have it posted on Facebook Marketplace and offered it to any agents or are you selling it solo? 

I assume that with the overage from the renovation, it probably ate into any extra contingency fund?

We also commit to going to our STR every 4-6 weeks and checking in, it is an extra cost but has bore fruit for us.

If I sold, I could be debt-free and have extra money each month to invest elsewhere.

This approach works well for wholesalers who sell deals to flippers, and flippers or realtors can benefit even more by taking the extra step to generate their own off-market leads.No one said methods like cold calling, direct mail, or Facebook/Google ads won’t help a realtor find off-market opportunities.Just a friendly thought, especially given the high costs associated with Zillow leads.