If you're looking at this from a distance, connecting with a local property manager could give you a clearer picture of what to expect in terms of tenant demand and property management challenges.Let me know if you need any more info or want to chat further about this.I hope that helps

But zero chance I would pay the extra to sell to this one buyer or expect debt to be forgiven. 

This is an expectations issue, not a calculation one.With that said, you need to be looking at properties where you can add units and/or bedrooms.

Here are some steps you could consider:Clarify Expectations in Writing: Send her a formal letter (via email and a physical copy if needed) explaining the importance of scheduling timely repairs and how delays have impacted the property and repair costs.

But the property as a whole was in much worse condition than expected, so I don't think the numbers would work out for me.

To do short-term rental, you need locational amenities and house amenities to win and that price point won't get there.Because with an STR I can write off  expenses against my W-2 income ( I expect a loss the first year) if it's an average 7 day stay or less.

Most lenders have a limit to how many draws you can take from your rehab budget and often it will cost a small fee (you can include that in your budget) so you'll want to confirm if/ what their limit is should you expect to be taking a lot of draws or complete the rehab in smaller increments.

Wasn't expecting this to come up. 

:) Its generally a good idea to know the condition of a property or level of expected repairs so you can anticipate those repairs and build them into your bid for the property.

One of my main challenges early on was learning to have no expectations and learning to help set and manage expectations with clients.