But realize that if you live somewhere seasonal, occupancy can vary... like cold winters in Texas probably equal lower occupancy.   

You won't miss the Chicago winters!

There are some decent spots that do well and are more affordable than Raleigh.Also I bought during the winter during slow season, great neighborhood but horrible photos, clutter everywhere, original condition.

Would love to purchase some place that has year round activities so income isn't limited just to winter.

From maintaining Winter and Summer temperatures to deposit alternatives, etc.

What are the main activities that attract guests up there...hiking, skiing in the winter? 

You can look into smaller FL towns - such as Lakeland and Winter Haven.

I am struggling till date with rehab not finished and it will only go worse since we are coming close with winter weather.

I also recommend talking to the tenants if you can, so you can find out if there are any issues with the unit (such as, "the landlord said they were gonna fix the a/c but they never did" - if you're buying it in winter, you may not think to check the a/c).Tenants always wait to see how a new owner will act so they can see what kind of leeway they will get with things. 

However, there is also a noticeable increase in tourists during the winter months, particularly around holidays and events.