I have been trying to educate myself on all things 203k prior to getting started, but the one question I can't seem to find an answer to is: If I plan on converting a SFR to a duplex or triplex, will the lender take into consideration the future rental income of that new unit when considering the amount I can qualify for?

The units were converted several years ago, it has been operating as Studios for quite a few years.

As to small multi-family possibly not appreciating as much as single family, consider an exit plan of converting units to condos, so they can be sold individually.  

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You could possibly get coverage on just the occupied units for now and a special coverage for the one under construction, and then convert that one to the same “occupied/rented” policy as the others once completed?

It's a 2/1 property and I will be converting it to a 3/2 property.

Cap Hill is a huge hub and I don't think you'll have a problem finding tenants and I'm sure your mortgage is already cheaper than any rent you can charge in the future.I have been converting my current residence (live-in flip and hold) into a 2 unit.

Eventually after 10 years of you don’t pay it back it converts to Principal again.

I have an AS is contract signed to purchase a 1925 bungalow that has been converted to a duplex for a buy and hold investment. 

When a gas grill craps out, convert it to charcoal using a welder, angle grinder and iron.