This would be some serious wiggle room for not only moving back to Chicago, finding a job, but then start hitting the pavement on purchasing.

This con job of a company took food out of my children's mouths! 

I lastly own my primary residence and have a full time W2 job.

We have a job opportunity that would put us in Tampa, FL about 4 months out of the year total (non-consecutively), and we are curious as to whether the Tampa market or nearby markets could be a good fit for us.

I'd also demand co-signers (parents, most likely), in case things go south you'll have someone with money who is collectible.2) There must be a plan for common area upkeep - kitchen and bathrooms get dirty fast.3) Competition around schools where I'm at is stiff.

You'll save money and likely do a better job than any company would anyways. 

What do they sell for, what are the common problems, are there different sizes?

However, your due diligence will not be refunded.If the home doesn’t appraise, if the inspection report is awful, if your financing falls through, if you loose your job while under contract, etc. the due diligence is still NOT refundable. 

Good job security? 

Most W2 employees will have a tough job justifying that more time is spent in RE activities but since my W2 is far from "full time" does that make any difference if I track my hours?