I have access to a lawyer for free to answer contract questions 7 days a week.You have to determine what your time is worth like anything else.

So KISS:- Use an LLC in the state you have a rental- don't do "holding entities" unless there is a very specific reason you want to do with a "holding entity"- Create a new LLC for new batch of rental only in relation to your personal risk tolerance - use an S-corp for active business and you will pay a salary (rentals are considered passive not active)Now in the future when you become a multiconglomerate business, then hire a team of lawyers and accountants to restructure everything for you.

My lawyer will most likely be charging that just to configure things, and she doesn't come with potential investors. 

Additionally, I starting a forum discussion called LLC Set-up:  Lawyer or do it yourself.  

It is acceptable to all of our lawyers as it has a certificate at the end.

Have a lawyer do it.

Hellow BP members,Does anyone in the Philadelphia area works, or know, lawyers that are very familiar with the establishment of LLCs and all the things that come it?

You can't speak to their lenders due to privacy issues.The lawyers will have to hash it out.

. - Anderson and Associates, they are your go-to here in KC for RE lawyers.

Of course, defer to your contract/lawyer for specifics.