One recent update is that he has traveling for almost 2 weeks and ignoring anything related to the transaction.

Lowering prices on slower days can fill in the gaps, and it’s also worth setting longer minimum stays in advance to mitigate low booking volume over time.In my experience, mid-week travelers are usually on the road for work—client meetings, interviews, conferences, that sort of thing.

That is a good point, and when I think of what makes me feel more confident in my first flip, it always has to do with mistakes around the rehab (cost miscalculated and time lines)  

You should never take a dollar from an investor unless you are 100% confident in your numbers and your ability to execute.

The 2nd unit needed some renovations which I have nearly finished and I hoped to rent out it out as a MTR to traveling healthcare workers.

Your thinking must align with the travelers, and often experienced-based thinking will take you much further than value based.So, let's say you are looking to enter the STR market and don't know what to look for in a winning home. 

I use travelers for almost all my STR policies. pretty solid insurance and good price

I want to feel more confident in my numbers and wanted to check with everyone and ask what strategies and software you use for calculating ARV based off of comps.

As for where to go, you need to decide what markets you would like to travel to and then narrow down from there.

.- Make about $65,000 a year before taxes (confident I will be making six figures in the next 2-3 years).- I work anywhere from 50-60 hours a week (I work in video production).- I would have roughly 35-40 hours a week available to dedicate to progressing my real estate journey.For me, the big appeal of being an investor in syndication deals is that it is not as time intensive as other real estate ventures, so I can focus more time into progressing my career in video production and growing my income there.