The Gingerman isn't bad and I've never been to Katy Trail Ice House. 

DO NOT BUY IN RENT CONTROLLED AREAS unless you can sell ice to an Eskimo or you have a lot of capital set aside for those buy outs.

@Allyson Gehring, Thats like asking for an ice cube at the north pole. 

You're skating on some thin ice here, so know your risks.

@Kody Veit Its so nice to see people throwing around 30-40k like its iced tea on a hot south florida day.

We look at appreciation as icing on the cake. 

Attached to the house (not structurally) is a decent sized cafe/ice cream shop which hasn’t been open in 5 years, but has everything needed to get it up and running.

@Anthony ConwayHow can I stay in shape but not watch the calories, because I like pizza and ice cream?

While I've had the cash-flow all along, I also have much icing about to be poured onto the cake. 

(We are installing a 50sq standing seam roof in the next two weeks) A newer option would be asphalt coated metal shingles, which are more expensive.I would recommend what ever your choice, that your make sure your contractor removes your old shingles, replaces your damaged decking, instals proper ice guard, and synthetic paper.