Now I see where the difficulty lies.

I personally have abandoned vrbo type rentals because the difficulty of compliance and the taxes associated are too high for my 3 or 4 units.

My take on the difficulty of maintaining both professions is that if you want it bad enough nothing will stop you.

After independence, the country was underpopulated and homesteading was prevalent - or else land was just taken from the indians etc. there are many advantages to having skin in the game.

Without an option, you have no skin in the game.  

Problem is, I may run into difficulties because while my car is registered and insured and my license is current and valid, everything is registered back home and not in Florida.

Hey everyone,I hope this discussion will reach people in the Chicago land area.As the title states my question is if in the general area of chicago, is flipping getting more difficult?  I

That makes sense and I understand not wanting to go through all of that trouble without some skin in the game so to speak.

Find an agent with thick skin, and expect them to complain about every offer you want to make anyway.My experience has been that about 90% of asking prices are way too high for investors, but make offers anyway.

We've done a few deals together already.I know what you mean about the difficulty in finding great deals.