Keep in mind that month+ rentals are usually covered by state laws governing tenant / landlord rights and responsibilities.

My realtor recommended a GC he’s used in the past for his personal properties.

I'd encourage you to keep metrics on everything so that you can see your KPI's evolve over time.

A lot of investors navigate this by using rental income to qualify rather than personal income.

What are the book keeping and occupancy tax challenges that are faced?

This is my first flip and the contractor continually keeps adding things here and there, and changing things slightly from his first quote.

If you still think its overpriced do some more research, what can you do if you owned that home to be worth even more, especially if you’re a DIY person.

This situation is such a long one but I will try to keep it short and to the point. 

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

If you can make 1% today you are doing pretty well, but keep in mind every property should be evaluated on its own merits.