I plan on learning as much as I can this Fall/Winter and diving in next Spring/Summer.  

I've never gotten away with just cosmetics on the properties I've done in that age range.Couple other random comments:You won't be able to do a 1031 exchange as someone mentioned.How long are you planning to take - guessing your sale would hit the market during the unfavorable winter months?

@Marc Winter  If you are asking about the house I referenced.  

@Elbert Dockery I'm hoping this winter things will get better for investors in Chicago.  

It is a ski resort and we get a fair amount of snow every year and it lasts all winter long.  

Early winter inventory is low and those out looking are serious buyers, so this is a great time to list.  

Gas and Electric bills from the winter months.

Californians in the summer and 'snowbirds' in the winter.  

It is a small, well taken care of beach cabin, two blocks from the beach, in a great summer vacation area... winter not so much. 

Problem is the upstairs gets super hot while the downstairs stays colder in the winter.