Does this sound unreasonable/am I missing something? 

The repairs you described do seem extensive, but for a property that you have faith in for the next 10-20 years, it doesn't seem unreasonable. 

It is unreasonable in my opinion to expect a contractor to “invest” in your project by covering material expenses.

If they are expecting you to fix everything that makes a creak, they have unreasonable expectations and you should probably hit them with the happy clause.

Do the math on the 401k for your situation, for most people having that tax savings now is a good thing and having diversity beyond RE is not unreasonable, but if your other loans are bringing in enough cash flow that you wouldn't be in a tough spot if one went vacant or the rental market turned, I don't see much point in paying those down.

Is it unreasonable to buy something 1000 miles from where I live and have a property mgmt company handle the day to day? 

If the judge grants the motion, the stay is lifted and the house debt no longer has the bankruptcy protection and the lender can pursue collection, including foreclosure.The Trustee can also file motions for dismissal for a variety of reasons, often the creditor has caused unreasonable delay which is prejudicial to creditors' rights or has failed to file required documents timely.Having said that, I would really not recommend BK investing for someone new. 

. $5,000 is not unreasonable. 

Not unreasonable considering you aren’t local it seems. 

It may be that someone else gets the property because you back out, but they may just not have seen the issues you do.You really don't want to get in the middle of a project like this and have to spend tens of thousands on attorneys' fees because the neighbor is unreasonable.