(Because of debt to income tied to property)-Will buying a home first make it easier to buy a rental?

So, a say $40k net income MIGHT let you borrow $150k (assuming you have no other debts/loans which I'm guessing might be possible if you have $30k saved up).So, the co-signer route is your best bet, just remember it may not be theirs since you will be tying up their credit.Hope this makes sense. 

May his girlfriend remain on the property as a life tenant? 

Interest rates likely to remain low - Interest rates will go up over the next 3-5 years, but I see no reason to believe they will go up by more than a a point or two.

Remain loyal.If you do find a fellow landlord (or anyone) who shares information and contacts, make sure you give them a proper thank you.

The owner is reimbursed by insurers then decides to demolish the remains and sell the land.

The owner is reimbursed by insurers then decides to demolish the remains and sell the land.

Only the cosmetic stuff seems like it would be directly tied to rent.

Do we have the current tenant move out, clean and sign a new lease with the new tenant with the remaining terms of the lease.

I am going to put a punch list together and address anything that is reasonable and request they put in an application to the tenancy board for a dispute resolution for remaining items that are unreasonable.