So the first is in FC, sale in 60 days.

It is my understanding that the minimum STR reservations are at least 30 days (also I see a lot of listings on AirBNB for 28 days minimum - why is that?). 

Quote from @Maggie Hamill: I believe the earliest date you can use is the day it was marketed as available, but I'm not an expert.

I am currently under contract on some commercial land near Houston with plans to develop flex space and have a call set with Hamza's team for 2 days from now.

Is your first thought “These things are the same and everyone else is just dumb for not investing in them.”?

Same could be true for every attorney in every state. 

I guess the bigger question is, does the income on Property 2 look enticing enough to keep barely breaking even in hopes of the day we can refinance it favorably?

Stop hanging out with your deadbeat buddies that spend all day drinking, talking sports, and otherwise wasting away.

Also spell out as much detail as possible in your scope of work with the contractor, you cannot assume that they are thinking the same thing as you when it comes to finishes and material choices.  

In my lease it states that the tenant, after 10 days, is responsible for all problems related to pest control.