Feel free to check out Petersburg, Hopewell, and Colonial Heights specifically, as there is Fort Lee, VSU, and Amazon right there so we've noticed a steady influx of people.   

If you are a real estate professional and more specifically, if the income generated from selling this property would be classified as ordinary income you would have a completely different treatment.

I'll check J Scott's book, but any Chicago specific knowledge would be great.

If you have a specific tax question, I recommend using the search function.

There is a lot of nuance to every specific situation.

They just want to be able to tell everyone they have a place in Aspen/Vail/Telluride.I cant speak specifics for other areas but here are a few examples for Telluride. 

I'd like to know if any of the other investors out there mind sharing their experiences with short term rentals in the KC area, specifically in Midtown near Hyde Park/Westport.

Highland,  IN to be more specific.

I should have been specific with the landlord or property Mgmt experience.As a lender, have you seen any consistency with what lenders consider or will accept as some type of “property Mgmt” or does it just depend?

Whether I purchase it cash or with conventional financing, the banks only want to lend/refinance up to a specific LTV (usually 70-75%) on the purchase price EVEN if I buy the property at a significant discount (e.g. 50% of its current market value).In the past I've always struggled with this same issue, and thus eventually I end up tying all my capital in properties and I'm unable to purchase more (even hard money lenders want you to put some skin in the game).