If we chose to convert it to rental, and keep all that money completely seperate from our personal finances, do we do it all in his name? 

And you likely haven't faced life on a downturn, it all comes down at once and it's kind of correlated professionally and personally. 

Another issue is these homes have standard 15-30 year loans in my personal name ..... so that is another issue ! 

People are generally referring to this type of entry as contra-expense or atleast that's how I interpreted.In the PA tax return, this line item was highlighted in Red and hence the question

They know how to track things, use multiple PMS softwares, file aircovers and so much more because I have personally spent years training them exactly how to do things the right way. 

I'm the principal broker for Hardin Realty & Property Management -- We encourage agents to invest and complete personal transactions!

In Philadelphia you customarily need a certification statement to be provided to the buyer and it appears the broker in this case is likely referring to form while redirecting the responsibility onto the buyer to obtain the document. 

Quote from @Jerryll Noorden:MAYYYYBE  interconnect 400 super comuters together and feed it every single piece of data on this planet and construct a real life emulator/simulater with every person's artifical character on that simulation where every user has inputter their life's journey...

To start, what area/location are you referring to?

My cousin has stepped up to fill the financial need, but I still will require in person guidance when planning the rental launch late this year or early next year.