From an income tax perspective, the LLC provides you with absolutely no benefit.Even from a "anonymity" perspective - if that is a Single Member LLC, the K-1 from those syndicates is still required by the IRS to be issued directly to the beneficial owner - you.If you don't make it a single member LLC, say your spouse is also a member, now you have a partnership tax filing - if it holds a number of LLC interests, it is now a partnership filing that is a pain to file to roll all of those activities in and report it on to your personal returns.In short...most likely it is best to keep it simple. 

Not quite as good, but it alleviates most of the pain.

What are any pain points that he has that you can help with? 

It is a pain but not insurmountable. 

The investor who presents to the ZBA without counsel doesn't come across the same way and the ZBA doesn't give the same leniency and patience if you don't address the correct standard for why the relief is sought. 

Unfortunately, I do own investment properties abroad that are still financed, so any lender that has experience with this would be much appreciated, the lack of experience in that regard has been a painful, and long underwriting process at first when I bought and then again when I refinanced my home a few years ago...

The pain is removing all HVAC, plumbing & electrical so you can sister or replace a beam or joist and then put them all back in.

Quote from @Gus Delgado: Currently looking into the DC market for multifamily, but seeing a lot of negative information related to fraud, TOPA, pandemic relief for tenants, etc.

Those landlords sometimes feels the pain managing property outside the state.  

@Neal Daftary-I think self-managing a duplex from 1.5 hours away is going to be a huge pain.