I didnt listen to Chad's podcast. So this if from my wine/port making experience.
A port yeast will give a better "port" style taste over the more oxidized and less sweet sherry. Mashing low will help with unfermented sugars and mouthfeel. I like that. The concept of using brandy in the wine is because it lets the grape juice "marry" the Brandy as they are both from grapes. Grain style is the way to go.
Commercial wineries use distilled wine in the upwards of 150proof and call that brandy. Its closer to Everclear. But because they come from the same plant they blend well together. The idea of "ice distilling" is a bad one, a legal but bad idea. You cant clear the methanol and separate the heads and tails out of a batch of ice hooch. Youre going to add too many fusel oils and off flavors. Stick to high strength Corn or wheat based booze. Of if you have any friends in New Zealand

have them ferment out an old oxidized batch of beer and give you the hearts of the run.
Racking over cherries and adding oak is a must and is no diffrent than adding oak and cherries to a porter or stout. The chocolate part ports have, you can get from upping the choclate malt to around 3/4 - 1lbs in a 5gallon batch. The tricky part is going to be color and fermentation temps. Getting the Purple red color may have to come from an addition of grape juice (as DFH does in there Noble Rot) and fermentation temps should be higher as thats where the "sherry & Port" yeast thrive...
Lot to think about here...
Pharmbrewer wrote:
Joe'Bronco wrote:
I would think that it would taste like highly oxidized beer beer with brandy. But since Grapes = Brandy wouldn't Barley = Everclear? So a highly oxidized, Everclear beer mix...

Oxidized beer tends to taste "sherry" like. Sherry and Port are very similar with port being MUCH sweeter. I feel it may be easier to get a madeira style beer than a port style as the yeast is what gives it its character.
Intresting concept...

I think Mosher tries to address the sweetness in the mash. He talks about doing a step mash at 122, 133 and then up to 167. As for yeast he recomends using a sherry yeast. There is also a substantial amount of alcohol added during the fermentation. I believe he recomends whisky or vodka. I've thought about ice distilling some sac mead I made and adding that instead just to keep the whole thing "home brewed". I think this beer would also require an extensive amount of aging.