The only caution I would say is not on the insurance side but on the sales side, if I walked up to a property and saw a bunch of patches on a roof it would be a red flag to me.  

Recently installed it (Red Rock Hickory) in one of my units. 

"House Hacking" is another way to go for you and can include rehab money needed as long you are willing to live on premises for a year.  

In the event of divorce she would keep all of her property that was hers before marriage - including your house if you sell to her.

Are you including cleaning of common area, repairs, pest control, and landscaping under maintenance?

I see plenty of future growth in these parts, and am eager to buy an old 2-flat or 3-flat (what the rest of the country calls a 2 or 3-plex).Everywhere I go in this neighborhood I see new condos springing up like concrete weeds, including several gargantuan buildings by the California train stop in an area that's mostly SFRs and small multis.My question is this: Is the influx of new construction a great sign for the rising prospects of the neighborhood or is it just creating competition for older buildings and rents?  

Please give me some input on the best educational tools or resources including information on MF and SF properties.  

Lots of things to consider including how much risk you are comfortable with.

Save yourself time and money, understand how to properly value a deal (which includes assessing the risk as well), keep it simple in the beginning. 

All of our properties are fully renovated, including upgraded electrical, plumbing, water and heat, to ensure low cost on future maintenance.