As for your specific scenario, I would encourage you to reach out to a professional to guide your tax planning activities ASAP.  

Yes, this should make a good rental.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...

At that point I dont know investing would make any sense, I have heard scary stories I was thinking about short term rentals but that needs constant cleaning after guests and conpetition is very high my friend spent almost 200k out of pockets to buy a property for airbnb and he got 17 bookings per year....

But i am here to learn, one day at time, one book at a time.  

My wife briefly help a friend manage their monthly short term rental in San Francisco while they were traveling and have a few friends that do it.Monthly rentals seem to book pretty well, but not at a significant premium to long term term rentals. 

VRBO does not seem to do the same guest verification or background checks as Airbnb and you have to opt in to Damage Protection (insurance or deposit) which I've read can detract people from booking.

Gill's book, but if it is proposing the same scheme as Mr. 

I have been reading Brandon Turner's "The Book on Rental Property Investing" and have learned a lot but wanted to get on here and ask for advice from everyone.  

I recommend reading the book traction and following EOS - they have a one page business plan that is awesome to follow. any planner can work it's a matter of creating the plan and how to monitor and follow through with it which eos teaches

Book a flight from Portland to Orlando rent a hotel and car and go to the planning department and building department in person and get to the folks that were running the permit and discuss paths to completion..