I am drawing new buildings for the Humanitarian OpenStreetMap Team. I am largely unfamiliar with OpenStreetMaps but love the concept and would love to be helpful with my free time. For cases where there are many smaller buildings (like at location 4.2483620, 96.3279390), is it conventional/okay to draw out these many buildings as single, large buildings? Or is the tedium of going small building by small building just “part of the experience?” (lol) I am happy to do the tedious option, just wondering what is conventional and what is preferred 
No, building=* areas should only cover the area of a single building.
If you’d like to represent “area with buildings” at a lower level of detail, then use landuse=* (such as landuse=residential).
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Especially as HOM is among others about disasters, it’s important to tag each building as an individual building.
Later you can add details about each buildings, like damages, roof material, etc.
If you odn’t have enough time, learn how to create buildings faster (Q to make 90° angles, copy/paste for similar buildings, creating a row of buildings…).
Hi Niccat,
As others have said, one OSM object per building. Most should be squared off (Q Key) or be circular. Sadly we get many odd shapes. 
As a new mapper, I recommend that you join one of the early-month London online Missing Maps sessions. They are focused on helping new mappers work on HOT projects with breakout for those using iDEditor or JOSM. The next one is 6 January. They are all on the OSM Calendar. Missing Maps London: (Online) Mapathon [eng] | OpenStreetMap Calendar
Maybe it is more useful to use the Rapid editor