They claimed the "rules have changed" and we would see a longer cycle this time.

Well many people Love PDX for the life style , Metro and cities have artificially crimped supply.. and that is not changing anytime soon.

The neighbor picks up garbage off the sidewalks, sweep it daily, pull garbage pails in, change bulbs in the common areas, and advise me if snow cleaning is performed.Given he's been there for 40 years, the condition of his apartment if you don't plan on upgrading is another $50 to $100.

There is no move In check list, so I am afraid if I make them unhappy with all these changes and they decide to leave, they could trash the place and just say everything was like that before (when I toured the home they had already blamed some things on someone else).Is this a valid fear?

This has to be disclosed to the lender which would change their debt to income ratio as they have a second mortgage on the home.

It will seem like an expensive month for your tenant because they will be paying $1,500 within 15 days, however, they have to keep in mind that they CAN NOT just have 1/2 a month for free because they want to change the rent due dates. 

from changing a number?

Im thinking of buying a second vacation home in the same area..does this change the need for an LLC?

Our next step is to find out if vacant or not (our realtor seems to think is occupied), offer a small $ incentive to said tenants to move out in a nice and tidy fashion as to avoid damage to the property (if not, start the eviction process), get utilities changed in our name, get title insurance (via taxtitleservices) /clear the title, then work on the rehab :). 

Does it change if I keep the property managers and I just inform the managers?