So it's not likely the fiduciaries would gamble on an assignable contract.

Buying real estate in California or any other high-priced market is more like gambling than investing.

Yes, sales prices in the FL market overall have increased recently - but betting on appreciation is a gamble.

I've always aspired to be an entrepreneur so I'm thrilled to actually make a go at it.  

If you can but there are a few arrangements thats need then sure.But NEVER invest with "need" money PERIOD, because then you blur the line between investing and gambling.

However, this is a gamble and we have put some nice upgrades on the house that might have to be redone before selling again

Maybe others that have gone through this can speak more to it but if it is with the City of Portland then expect that to be a pain and to cost a lot with the gamble that they don't approve it.4.

Starting and building my business was a thrill, but now that its going and I don't want to expand further, my creative business part of my brain needs a new venture!

Typically expectations for NPNs by newbies is unrealistic and what they think they are investing looks more like gambling.  

I feel like I'd be taking a gamble with it.