From asking around the community, it is difficult to find cash flow under the current market conditions.

Regarding a refinance on a sub2, are there any special conditions or is it straight forward like a normal refinance?

A savvy qualified buyer would condition their offer on you replacing the full roof.

The two biggest challenges I hear are not realizing the condition of the property (for example, finding out the property is in a worse condition than it is) and working with contractors (not finishing the job, taking too long, etc).

The guest said she was house hacking but only stayed there in the property 6 months out of the year and short term least it out the winter months to travel and stay where it is warmer weather.

I'd make sure your comps are very similar in layout and condition, similar updates, etc.

I found myself missing out on more fun occasions than I'd like to admit because I needed to be at my properties handling some issue or showing it when vacant.I found that I had become conditioned by the sound of my phone (even though I helped alleviate it by having quiet hours on my phone from 7:30pm - 08:00am). 95% of the time when a tenant contacted me, it meant something was broken, there was an argument, or there was an excuse about late rent.My husband has been gently pushing me to get a PM for a while.

If the owner is happily paying for repairs, the PM gets paid, the owner improves the value of their property, and the tenant now have improved living conditions.

Some situational pressures are a somewhat wobbly rental market due to economic conditions (Nike/Intel layoffs). 

However, in today's market conditions syndicators that are pushing a hold period under 5 years would seem to me that they are being too aggressive on assumptions.