Good morning,So far this year, I have contributed $12k to my 401k. 

BTW - this forum has been excellent and I want to thank everyone that contributes.

If you suggest New, LLC should he make a contribution from the Old, LLC to the New, LLC and if so what are the tax benefits?

I am being told that many “wealthy” investors do such a thing.Again, buying a property is not an expense no matter who is on the receiving end.If Company A purchased it for Company B, company A basically just gifted it to Company B and Company A will need to pay gift taxesIf Company A gave money to Company B, Company A either Loaned it or Contributed as Capital/EquityCompany A cannot expense it, because it isn't an expense. 

This is a great group of people, and I'm confident you'll find tons of support for all your questions as well as a place to learn and contribute your experience.I think your question about a business option is whether you should get an LLC or purchase properties under your name.

Another thing to keep in mind on how much cap gain you contribute: if you are spending your $100K to buy an existing property, you also have to spend enough to double the basis in the building.

For this reason, we have started a collaborative spreadsheet for all to access and contribute. 

Whenever you have a W-2 job that offers a 401(k) plan that matches contributions, max that out.

In terms of structuring, an issue that has come up is how do we handle the transition from holding one property to holding several, especially if the members of this business have varying levels of capital to contribute at different times. 

That is the very definition of "highest and best use" and will make a lot of folks $$ while also contributing 8 affordable units to the city of Chicago.