I definitely could have done proper inspections, and made the mistake of relying on a contractor's appraisal to both identify issues and get a quote, and he then missed things.

If you want to expand, I'd identify the deal, market, niche first. 

We've identified that we'd like to start with some multi-family properties, 2-4 units, and we may even do some house hacking (not sure - the THOW rent is already so good!).  

I'd start by identifying your WHY and then moving forward from there.Good luck!

So far, I've started working with a real estate agent I think is great, and also believe I've identified a property manager that I think is a good fit for me.The agent has been bringing me deals that seem to fit my parameters.

If so, and the title commitment identifies those encroachments as specific exceptions on the title commitment, you would say "Not acceptable. 

If they were that bad you should have identified the issues while you were inspecting the property.  

Good stuff up there.With me, especially because I've only accrued about 12 months experience in Chicago where we are buying right now, anytime I cannot identify true, apple-to-apples comparables, I might just pass on the deal altogether.Especially in Chicago where you have several types of homes (bungalows, ranches, cape cods, georgians, etc.), you really cannot comp one with the other unless it's the same style.Here are some general tips when comping homes:Never cross any major highways, and try not to cross any major streets if you can.

This way the IRS will receive the 1099-S and identify the transaction as occurring within the tax-sheltered plan.

You have to identify what your goals are and set parameters that get you to that goal.