Let's be real, if average lenders and realtors can understand it... it can't be THAT complicated. 

Your tenants will of course put up a fight.3) From an administrative standpoint, it's much more complicated to keep track of each tenant's annual reconciliation and base year expenses (I manage the property myself).  

All-in-all its a buyers market2)  Unlike in SFR multi sellers tend to be other investors and are more sophisticated which again makes it harder on your side vs. getting inventory from homeowners who will always have more complicated factors. 3) You may not like this one but think about this from a seller or brokers point of view, why would they sell to you.

I hear there can be many complications or trouble getting funding if I put it under the LLC initially.

There are always complications, I'd recommend @Denise Evans and her book on Alabama tax liens.

Its complicated and IT DEPENDS.  

If your son is the end owner why are you bothering with the complication of having your name involved at all.

. $1.4M.Now- here's the complication - We just bought a bigger house #2 (our new primary residence) - for approx. $2.5M - with 20% down.

It can get complicated.  

Being an investor, on the other hand, not only helps you to expand your knowledge about the industry, but ultimately opens your eyes to more non-traditional buy/sell methods, which may provide additional income generating / wealth building options.The only caution I have to getting your license is that, depending on your state, it may open you up to some legal complications.