There are a lot of good posts on here so I would take some time and read the forum so you can hit the ground running.

This was the very first time they had rented it; brand new landlords.

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

He can spend the next few years-ish getting a finance degree through an online school while working part time, but he just got offered a full time position helping with sales for a local wholesale real estate company. 

I don't want to waste anyone's time providing quote after quote for me for the properties I am merely in the analysis stage with.

With one duplex you should be focused on selling 99.9% of the time and .1% on the duplex.

As you get deeper into your career you will of course need to spend time servicing these leads so you will have less time for prospecting and lead generation right?

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software. 

Thank you for your time and patience!

By the time I received the subsequent emails, I stopped reading them because I realized they were of no value.