Some cities, communities, neighborhoods, etc, don't allow short term rentals (some HOA communities for example).With that said, I don't see why it would be a problem.

Stay in your job if that is what you want, but quitting your job in a relatively short period of time is possible. 

Based on what you wrote, short of paying cash, that's your only option.

Others might be fine with taking risk, but least by doing this a person can get an idea of what might go wrong.e) Legal document analysis: it will usually take a few days to go through the legal document properly, as almost inevitably there are tons of gotchas that either have to be explained, or mitigated with a side letter.That is the very short summary of what I do.

Ask anybody that has a true background in these sciences.In short, tobacco involves burning something. 

Very excited to be jumping in.I think the biggest question perhaps in the short-term is how much do I have to lose if I do *not* get everything completed before losing my active income source?

One CAN figure out approximately how much a property sold for even if it's not listed in the records:  extrapolate the transfer taxes (state/county/city) and multiply out.Just an aside:  I remember back in the day when the appraisals were coming in short in an appreciating market (something like we have today) we would ask the buyer to pay MORE money for the transfer taxes (no law about not paying more taxes) and it would help show a higher "sales" price and help 'push' up the comps--not recommending you do that now--much more data available for all eyes.But I would recommend that you buddy up with a like-minded realtor, and work out a mutually beneficial arrangement so you can get the info you need, and they can get listings, sales, referrals, etc, that they need.Better yet, get licensed yourself and get to know the business from the inside out!

Its not assured you should just hold on always and forever.In short, RE is much like other forms of investing.

I think missing over it is an easy, short term fix.

Not a bad jump into investing option with the intent of a refi a short time later.