Establishing a proper portfolio structure

[Cameron C.]

I understand there are a variety of forums, many of which can address my situation to a certain extent, however, I thought it would make sense to lay out the exact context of my situation.

I am getting ready to purchase my first investment property (first property altogether actually - currently rent) in Pittsburgh, PA. A friend and I are going in on the deal and decided the first step we should act on is to establish an LLC to purchase and hold the property under. I have plans on buying more properties in the future, which I assume setting up a separate LLC for each would then make sense, however, I want to be very cognizant of a few different strategies / approaches up front so that I can be nimble and flexible with my portfolio for years to come. With that in mind, here comes my question...

In your experience, what have you seen work best for a portfolio of properties, many of which you may have different partners and different legal structures in place? I'm wondering if continuing with the "one LLC per property purchase" rule makes sense or if there is something else I should consider? The other piece of this puzzle is from the financing perspective. I'm wondering if and how I should set up a separate business banking account to be able to maintain these properties going forward in order to avoid the co-mingling of personal and investment funds. Would it make sense to have a separate bank account per LLC then? If I followed that mindset and in a few years I have 10 properties, 10 LLCs, and 10 business banking account with 5 different partners I feel like that might be an absolute nightmare and ongoing headache. I want to make sure I'm thinking about all of these things up front so that I can be flexible down the line. Does it make to have one business bank account and federal tax id and if so how can I link/associate that with a variety of different LLCs? The other biggest concern I have that I want to be thinking of is how all of this comes together from an accounting perspective. As a part time real estate agent who also have a W2 at tax time I already understand how complicated multiple incomes can be. I'm wondering how I can structure all of this while keeping it as simple as possible.

All and all, there are many questions baked into this post but I would greatly appreciate some general guidance and/or advice of where to start.  There are so many components that can make or break your success in this business and would love to hear what has worked for others and see if it may be applicable to my scenario.  I'd much rather put more time in up front thinking about the foundation of my strategy and investment structure than piece together a variety of broken parts down the line.  Any and all info, success stories, nightmares would be appreciate to help steer me in the right direction.  Thanks BP community!!