How does it work when the previous owner agreed to consolidate all that debt?

When you know who is the most cost-effective, put them under contract including their exact scope of work as an exhibit along with a construction schedule that you both agree to that they initial as a separate exhibit.

Agree though, compnaies getting things off their books is more concerning than price (in a way)  nice deal and like you said, it was because of your ability to act quickly.  

Has it has already been agreed that he is moving out at the end of June?

If you are nervous about not being able to see your investment, or you'd like to learn the ropes by being involved in the rehab, tenanting, and management processes (more a DIY approach than turnkey), then I agree with @Lane Kawaoka that perhaps you should look more closely at your own backyard.

I contacted the owner and at first he insisted it wasn’t his responsibility but since I had notified him and we are neighbors, he eventually agreed to pay half of the tree removal cost, no insurance was involved.

I asked that they take care of most of these items, which the team agreed to, but with there now being a tenant renting out the property (this wasn't the case at the time of the inspection), my guess is that it's going to take some time for these things to be addressed.

I agree with Brian although many portfolio lenders would lend quickly if you have 20-25% to put down. 

However, we do change the locks with each new tenant, that way they are the only ones with the key accept management.As for changing the lock on a room you want to rent, you would have to discuss it with the landlord and have then agree.

While I agree with that sentiment, neither my friend nor me are local to the vacant land parcel.