I need a second pair of eyes to take a look at my numbers. 

Second, if you own a business with a partner and die, your spouse is now in business with your partner and he or she may not be the best architect, electrician, dentist, or otherwise know anything about the business.

Second, I hope you're using an experienced facilitator!

I am looking to buy a second multifamily in Chicago, I have been searching far and wide and it seems that I can only afford the higher crime areas of the city.

That would require us to empty out a unit with a perfectly good tenant, move into an apartment that we don’t want to live in long term, wait until our desired unit is available, kick the undesired tenants out after a year, and move for a second time...

I'm not an attorney but my understanding is yes, you can definitely do that, and I believe things like that happen every day.While I can see some possibilities for why someone would want to set things up that way, I do have the instinctual thought that it might be over complicating things.Technically the second LLC is another layer of asset protection, and maybe you have a very specific entity structure setup for taxes which would make it beneficial to do it that way (an LLC inside an LLC), but it's worth asking the question of whether these is much difference, or much more protection, than just having you (presumably a Mass. resident) be the member of the RI partnership LLC straight-out rather than having your MA LLC be the member.Also, depending on what else you have going on in your MA LLC it may be a disadvantage to have it be a member of the RI LLC from an asset protection perspective - if someone were to be able to pierce the veil of the RI LLC then everything in your MA LLC would be at risk.If you do go with the MA LLC as a member of the RI LLC, when you go to sell the property you'll have non-resident withholding - but you'd have that if you personally were the member of the RI LLC as well.You'll also need to be careful how you sign anything relating to the RI LLC - you'd have to be careful not to sign as member of the RI LLC but as member of your MA LLC, member of the RI LLC.

My father passed a few years ago and my my mother is aging and she has asked me to help her with a rental property she owns in New York City, Queens to be exact. 

My father just told me that he had built when I was 5 and paid $26,500 , back in the early 60's is now for sale of $610,000. 

They seemed to be happy and they nodded in understanding.THE SECOND MONTHSomehow during the second month, when the newness wears off and the happiness falls into a routine, the new Tenants become confused.

We only have a house or two, we say.And just because we got away with not having a professional layout when we received a mortgage for our first rental or even second rental, we think it's okay just to present a mortgage company, bank or hard money lender, just some figures written down on a piece of paper or on an Excel Spread Sheet.But what happens when the time comes when you want to really expand?