What the second contractor is proposing sounds pretty good, but could easily lead to an iffy installation down the line in 3,4,5 years. 

sounds good in theory but lead Generation cost money.. and you have to really look within to see what your skills sets are.those that do well in this business ( see a bunch of them) are like any other well capitalized and run company.1. they have a marketing budget which is anywhere from low of 60k a year to high of 500k a year.2.

A property management company has approached me to partner with them so that they can start managing short-term rentals in addition to the long-term rentals that already manage.Their role would be the boots on the ground dealing with turnover and maintenance and I would handle pricing and guest interactions.

and lead me to wanting to learn about passive income, and acquiring financial freedom.

The main thing you need to focus on is converting leads to clients.

My goal was to buy single family homes in distressed properties ( short sales, or NOD leads by calling home owners and seeing if they want to sell before they go into foreclosure)  in a growing population area with strong job growth and buy, add value , and rent them out for tiny bits of cashflow and wait for appreciation. 2 main questions I have at the moment. 1) How did you pick your market to buy your first investment? 

The returned mail pieces are the best leads to follow up.....the dozen other people mailing them aren’t reaching them either. 

I am utilizing PODIO CRM for staying on top of my leads and ensuring I process them to closing in the most efficient way possible.

What I'm generally looking for is for a filter or some software that can produce a true list of "For Sale By Owner" leads. 

that works.. when you get a lead send them straight to the lender to get qualified once they are sell it to them.. same as any other transaction..