There are a lot of great opportunities in the general Chicago area, can't wait to hear about how you're tackling them.See you around the site.

Since I am trying to get started in wholesaling or assigning the contract, how would i tackle this problem?

A little extra temporary cash flow might help you tackle some of the upfront costs of being a new property owner.Given your scenarios above, I would also opt for the duplex.

What area, neighborhood, city, will I tackle and make it my comfort zone?

As I've played around w/creating a business website, I found myself wanting to publish two sites: one for motivated sellers, and one for potential investors (private money folks).I wonder how you all tackle this idea, that there are multiple facets to our business, and the message we have for one group is not appropriate for the others.

Let's tackle the 401K questions.

I would consider them practice more than anything else but now I think we are ready to tackle this thing and create a portfolio.Our plan is to flip at least two properties before purchasing one or two multifamily units in the local market.

Should I tackle this myself or just buy it flipped.

Did you hire out everything or did you tackle any of the work yourself?

There's nothing like total immersion to become Baptized as a landlord IF you're willing to tackle the tasks at hand.Here's what you'll need to do in short order:Crash course on landlord/tenant laws in your stateSet up (separate) systems for marketing for target tenants, screening/vetting prospects, easy rent collection, bookkeeping, contractor/handyman management, etc.The three best educational resources I can offer:Fixer Jay Decima, of 'Tenants & Toilets' fame (lower-end), Mike Cantu for mid-range tenant management, and David Tilney for the higher end of the market.