With regard to your specific question, I am a huge fan of paying cash to sweeten your offer (seller's don't like contingencies), and to speed up the process. 

2) If you have been through the street vacation process, what were some of the was in which you were able to speed up the process?

Hedge funds are very good at the stock market with speed trading.

More details needed to offer advice: Monthly Mortgage Payment, outlook for speed of getting it rented, type of neighborhood (A,B,C,D)., what Cash Flow do you anticipate, etc.

If you’re lucky, and network on and offline, you might find a mentor (their hard to find) or two to speed up the learning curve.

I'm in Central Oregon which is one of the hottest and fastest growing markets in the country and that has a lot of people feeling optimistic, but I like what you said about those extra expenses and how quickly they can add up.

But overall a great place to live.No state income tax, great job market, warm weather year round. 8 our of 25 of Forbes’ 2018 America’s fastest growing cities are in Florida.Brian

You may not want the liability/headaches that come with being a landlord so rentals may be out of your interest whereas if you are just trying to maximize profits and earn cash in the short-term, selling & flipping could be more your speed.

If you hit a speed bump I’m confident you can overcome it from your statements.

We can purchase real estate the fastest with an FHA loan and then refinance later to a better deal.