Some places you can get away with 2% of purchase price all in for closing costs, other places such as where you have a large amount for transfer fees, you could go as high as 10%.  

So i'm acquiring my units at a large discount.  

Not my cup of tea, but Boston has a lot of great things going for it that in the long run I think you could make it work.If by multi-family though you mean a 5+ building that you're presumably going to look for in the Midwest or South...it's in its own bubble as a disturbingly large number of people who made bank in the last 10 years of the up market are shifting their focus to a larger scale asset and are purchasing these distressed properties which is driving cap rates down because people need a place just to park their cash. 

@Shane Gaboury I would personally stay away from any condo investment because the economies of scale (only 1 - 3 doors), the special assessments that you have no control over and this is a speculation play.

Maybe rinse/repeat the process until I’m where I need to be, establishing and scaling systems as needed.

This is because it is largely tourist based and in recessionary times, one of the first things cut is discretionary travel.  

My focus would mostly be focused on people who want out of there current situation and are possible looking to scale down to a more affordable option.

I would certainly suggest looking into large multifamilies if you want to get there.

The short answer is that you can absolutely do a cash out loan on an investment property but working with any large bank is out. 

A little more about myself - I've been in San Diego since 2011, graduated from UC San Diego, and now work for a large commercial General Contractor.