When meeting for the holding deposit the prospective tenant was 40 min late due to work and not being able to find place to get a money order.

A prudent investor doesn't seek quick riches through shortcuts.

Great work, and I’m sure the investor was thrilled with that outcome!

You just have to find the properties for them that need work and get them at price that works for both parties. 

I have a great general contractor and agent that tours the homes, does the work, and finishes up punch list items.

Regs can run the gamut:  STR licenses are unlimited and available immediately with no restrictions, STRs can only be rented so many nights/ stays a year, STRs can only be in designated areas, the number of STRs are capped and there is a waitlist for a license.As others have mentioned, typically an unregulated STR will have more revenue than a LTR, but it will require more consistent work and effort.  

Agents are trying to take a shortcut, especially here, and that is part of the problem.

@Yosef LeeThe personification of hard work, and dedication.

I imagine there is a lot of work and things that need to be sorted during the day and cant wait for the weekend. 

If the second property you are buying is not turnkey, will require some work, and there is a clear value/range of what you can bring the property to by adding value then you can refinance to pay back the majority if not all of your HELOC (used for downpayment or to buy the property completely).You'll need to know how to analyze an after repair value of the property to figure out if that technique can work or not.