Any grey-based colour choices - even richer ones - externally should work.

If the building has a heritage designation, or you simply wish to preserve the elaborate external trim or dentil or internal mouldings, these things are time consuming and skill sets to restore them, uncommon. 

for some one who can do it ( IE live with their tenants) and the market allows it financing wise I think house hacking a FHA deal your first one out of the gate and keep as much liquidity as possible is about as smart an idea as there is in todays space.Not everyone can live with their tenants though.and if the state or City does not have ordinances to the contrary another great thing about house hacking a 4 plex that many don't know is you can totally choose your tenants.. your not bound by the laws of fair housing.. its a federal law that you can as long as you live there absolutely choose who you want to live next to you without any repercussions of discrimination against any class.But do check with your state or city to see if they have any rules themselves if not.. you can really set up a 4 plex nicely by handpicking your tenants .. then when you move on you only have to find one more within the normal rules.

HOA covers the external of the building, not internal.

It is not a major issue, no more that a extended power failure due to external issues.

That's functional & external obsolescence.

At the very least get a roofing company to examine the roof externally and internally for possible issues.

They were not hand picked tenants.

As far as analysis, look up area job growth, cost of living, and main area industries for external influences.

Transfers between Chase accounts process immediately or within 2 days depending on the amount, time of day, etc otherwise it will take 4-5 days to process with an external bank.