Are there any specific things I should know or be weary of before I begin this journey?

I won't presume that they shouldn't have done this, but will state that in most jurisdictions with rental licensing laws thats a big no-no.To answer your questions generally (not specific to Colwyn Darby, PA because I am not licensed there):1) Generally the county will not allow evictions or rent collection actions if a unit is being rented without a licenses.

If the idea of this specific type of deal could be mastered and then scaled.

Second, will you owe transfer taxes (that is very state, and even city specific sometimes)?

About 67% of people responded Yes", with another 15% or so saying "Yes", but only in specific neighborhoods. 

I'm wondering if any landlords in Portland, OR can share the screening criteria they currently use.

Buy with a specific buyer (or group of buyers) in mind.

That said, this all depends entirely on your financial position, investment criteria, and what you consider a good deal. 

., work related supplies, travel, meals and entertainment) are not considered wages as they are provided for offsetting a specific expense incurred while performing a service for the employer. 

Sue for specific performance, sounds like they aren't adjusting the price.