I think you may have your understanding backwards as a very common strategy is for people to contribute to their 401(k) through their employer to get the full match, and then roll those contributions into a ROTH account at the IRS maximum per year (currently $7k).

Transition from employee to employer.

That is real estate investing.Some people might call wholesaling a way to get into real estate investing, and you can technically do that without any experience (whether you are successful is a whole other can of worms, but you can spend a lot of time).Becoming a real estate agent can be done straight out of college and a lot of agents are real estate investors.But anything self employed like wholesaling, flipping or becoming an agent will keep you from getting loans too.  

Hi Jesse,In my personal opinion, since the primary reason you are doing the work is for the benefit of your employer rather than for your own rental properties, I would be inclined to say no.

Seek out regions that are seeing increases in infrastructure, employment, and population expansion as these factors can eventually raise property values.Pitfalls to Avoid:Overleveraging: Take care not to put too much debt on your shoulders or overextend your finances.

FedEx and Eli Lilly are two of the larger employers.

I'm searching for an insurance professional to discuss the concept of negotiating group purchasing property insurance for a discount (similar to what is done through health care via employers).Are there regulations that would make this prohibitively difficult in the property insurance industry?

My spouse and I are members of the LLC - so do we still need EIN if we are not employing anyone?

Your greatest challenge is going to be running this management company without the appearance of co-mingling all of the LLCs together.Bear in mind that one of the things that you'll be doing here is converting Passive Income to Earned Income via the Mgmt Company and that will be subject to self employment tax whereas had you left everything in the property LLCs, you'd have only passive income. 

@Alex JacobsNew investors who want to increase their portfolio and reduce their initial investment often employ the "house hacking" method.