I wanted to report back my findings on this experiment. Pretty neat actually. So, BrewFather would not figure in the wort condensing factor of an extra long boil, regarding gravity (only higher SRM). Naturally, the longer you boil the less volume you will end up with. So what I did was scale up the batch size (not just water, entire batch size) to a 7 gal batch. The end result was very interesting, and now makes total sense.
Target OG (per BrewFather)- 1.080
Target FG (per BrewFather)- 1.017
Target ABV (per BrewFather)- 8.3%
Actual OG- 1.095
Actual FG- 1.030
Actual (assumed) ABV- 8.6%
Conclusion- Scaling up the entire batch, and condensing the wort with a longer boil left me at approximately 5.5 gal in the fermenter, of higher gravity, thicker, yet less fermentable wort. Still nearly hit my target ABV, it just elevated the entire spectrum.
Cheers!