I’d say 90-95% of the time, quotes come in extremely reasonable and the work is done properly. 

It's been my experience that most tenants are reasonable and understand that "magic repair fairy dust" doesn't exist.  

Good luck getting Chase to hear you out.This is one of the many reasons that it's best for W2 earners to start slowly as investors, not to say that you aren't doing that, but in general, the learning curve is great.

As an investor, it's often difficult to qualify for traditional mortgages -- for this exact reason.

It's a small home so there's no reason she should have taken so long with everything.

But more than likely the bank won't want to sell it as a flip and if they did you would need to hold on to it for a period of time till you could sell it (or an LLC that is the owner of the property).My best advice is:  You probably will need an agent (more credible that you), find the reasons its worth the price you are offering, and build connections with the bank (meaning constantly following up). 

There certainly can be reasons - divorce, job loss, etc.Good luck and let us know how the meeting goes tomorrow!

A stress-test does not mean use reasonable expectations, it's a test that uses extreme events to see how well a portfolio could hold up. 

You probably should be operating and owning your properties in some sort of business entity for many reasons.

Were you able to locate reasonably priced medical insurance?