I know a guy who carries his in the inside pocket of his coat.

You can easily end up with the building equivalent of a beautiful suit coat but no pants. 

There are no sugar coating things at BP my friend.

Starting off with house hacking seems to be a good route if it fits your lifestyle...anyway, I bet you've come across the White Coat Investor blog/website...in case you haven't seen that yet, it's really good for MDs.  

From the start, it was bad but now the windows are simply falling apart and the Low E coating is coming off.  

Cosmetic could mean a coat of paint or it could mean everything's there but beat all to hell - cabinets old and tore up, holes in doors, etc. 

Joel Stell if your planning on repairing the drywall make sure you put up one coat of primer just to seal the tape and joints.

A new coat of paint with a good scheme can make just about any house look brand new and even painting the front door a color other than white or brown can make a big difference.

It took me about 2 -3 hours and about an hour for the 2nd coat...

A HELOC should be explored in addition to a cashout, lots of variables here as to what the best route is.I wouldn't put much weight into the neighbors, this is common and as investors we build thicker skin as we go forward via pesky neighbors and tenants. =)I would recommend your plan involve you not paying MI on your new purchase, so coming in with 20% down + would be my advice.