Imagine buying an old crappy duplex and having to put my money and time into rehabbing it and keep paying more out of pocket to maintain it, AND having to compete with all those newly built townhomes down the road.

I would take good photo of a finished area and post newly decorated, or something similar.IT WILL RENT !!

But this is really something they need to fix, and at least offer the same features as on airbnb (no instant booking with newly registered guests with no reviews, for instance, as a host's option).

Since the others have answered your question regarding pulling out cash on a newly acquired property, (BTW - its called "cranking" a property for cash) I will address the benefits of seller financing.

A scheme that was only launched once my wife informed them of the cost to break lease.Any experienced input here would be much appreciated.Ken

How do you think is it a good idea to launch such online service in Chicago and in the USA in general?

For example, it has to be a newly formed LLC, all investors must fund the LLC at the same time and no further capital contributions may be made by any of the members.

What are pros and cons of newly built property and previously owned ones? 

I am possible looking into paying cash for some new Golf and Country(Spa, pool, tennis) developments launching this year.

Earlier this month Tezos dot com raised $235 million in a Crypto Curreny enity now others are launching as well over 700 Initial Coin offerings some in Clean tech others in Real Estate like the token market announces new ICOs. http://www.crowd101.com/top-5-crowdfunding-platforms-equity-investing/https://tokenmarket.net/blockchain/ethereum/assets/real-platform/