As you have experienced, trying to predict what will happen through the course of two years is very difficult - contractor integrity, materials costs, what the sale price will be, what the rental price will be. 

I have seen that creating a site through a PMS is not a good idea since it makes it difficult to chnage PMS in the future and you may not have the full rights to your URL.

not saying it can't be done, just that it's difficult. 

I do realize that the climate has changed since this question was posted, however, selling a note in good standing in these times should not be too difficult. 

If landlording becomes “too difficult” for you, buy different properties.

It's simpler to act as a sole prop for that income stream.The "comingling" event is a difficult to define concept for me.

It's very difficult to get any good inspection done without virtually all of the furniture, wall hangings, stuff in closets and the like gone.

Condos are difficult and expensive to insure here.

The mortgage business is notoriously difficult, investor and lender guidelines (bank rules) are complex and vary among investors, generally speaking, brokers are not lending their own capital and the liaison on concierge gate keeper. 

They did a good job for us in a difficult eviction.