Sometimes if you are renting the unit and it is not insulated properly, then you hear footsteps and conversations from next-door units, so tenants complain a lot, but there is not much you can do.Also, one time the unit above mine leaked water into my unit, and the HOA said I needed to talk to people living above mine to fix the issue and they didn't have the fund to fix the bathtub from leaking into mine, so I had to pay for the repairs.Sometimes working with HOA and is painful, but other times is easy if the unit does not have problems

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? 

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...

It is a pain but not insurmountable. 

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.

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.

Which ones are the most painful?