And they can only look at the specific work that was done . 

@Jonathan Krystinak...I second Orlando, and our area has tons of properties that are designed specifically for for folks who want to spend some time here, and rent them out the rest of the year.

But if you're not wanting to go the off-market route and your cousin is unwilling to accommodate it may be worth finding another agent, specifically one that is investor-friendly. 

Is there any suggestions on WIFI providers for landlords to use specifically for a security system.

Those are all computer algorithms that can't take specific details into consideration like paint color, flooring, countertops, room layout, quality of neighbors, and many other factors.Use their numbers as a beginning analysis but then actually look at comparable rentals on the market and compare them to yours.

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.

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

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