Honestly, I think the biggest hurdle you are going to have to overcome is a lack of time. 

When you get clients these will be the biggest pieces in providing value. 

Taxes and insurance will be the biggest variables on the expense side. 

Yes absolutely to start off I am looking at 2-4 unit multifamily properties.The part where you mentioned about going out into the market and not just sitting behind a computer screen, that's one of the biggest things that has kept me from making any significant moves so far.The first thing I want to learn is how an investor analyses a property (not only using numbers, but qualitatively), and I think going out and looking at real deals and talking to investors is the way forward.Thanks a lot for your response.

What are the biggest hurdles with purchasing in a state that is much further away (Midwest etc) and is it smart for a first property?

There are pros and cons to each set up but the biggest con of closing in a LLC is it typically requires business purpose loans that have less advantageous terms than conventional financing.

The biggest issue with ADUs is small units in small count is very expensive development.  

Some of the biggest complaints i see are that you have to use specific contractors and it may take awhile before they can come out.

The biggest thing I can't get over, is the new agent objections.

At the end of the day my biggest regret is not buying a duplex to a quadplex with a FHA loan.