If I cannot break the lease because I want to sell or if property is sold, would it be wise to renew the lease for 6 months at a time?

While I was in business school many years ago, one of our teachers said something so wise it stuck with me since then; “Your business can only grow as large as the work you can handle”, or to modify what he said; once you run out of hours in the day your company will cease to grow.

First, what is your goal income wise?

I'm considering relocating and investing here & am curious what cities are looking the most promising, real estate wise.

And given that such a crash is a real possibility, then it might be wise for a Newbie to wait-n-watch for how things transpire in the housing market in the next few months, while looking for opportunities in buys, that might occur in such a possible crash.

Past that, cashout refi is also viable if you can afford the new payment AND will get those funds wisely invested. 

(after I get my $ out with interest) Wise words, Sue!

Just thinking that a 500sqft flip is relatively low risk, cost wise.

My vote is to continue doing what your father has done and use his advice wisely.

Very wise.