If I can't though the wife and I are planning on moving back in, putting a big luxury kitchen in and waiting until we qualify for homestead again before we attempt to sell it.  

It's their job to sell loans, so they won't mind talking to you.They can also give you a ballpark figure so you have some idea about how much you can borrow and what price range you can look at and actually have a real chance to purchase.You might be able to find a condo developer who is offering a financing package on a new conversion; especially if it isn't selling as quickly as they hoped.You are probably going to have to start with a much smaller and not so luxurious condo.

There is an article in today's Crain's Chicago Business about investors flipping condos in downtown Chicago.  In on example, an investor buys a 1960 sf condo in Olympia Center, a 30-year old upscale high rise in a gre...

If it were me, I'd wait until the tail end of of a recession to buy in vacation rental area IF that's something you desire to own.

My management company knows to call me first, I can decide to go myself, send my own guy, or let their guy go.I've had to use their guy when on vacation twice and they charged me very little.  

Can pm on Monday when I return from vacation thanks.

@Jen FaulknerYou may find more information if you look up Short Term Rentals or Vacation Rentals.

The only issue you're going to have is that you'll have to document why the new home will ideal as a primary residence while vacating the current primary (larger home, larger family size, more rooms, better area, etc).

These are basic 1 BR condos, not luxury units, but nice enough.  

I am thinking that when I close on December 4th, I tell the current tenants on the first floor that they have a 30 day notice to vacate the unit so that I may live there.