As for the permits, they will be fairly easy to get and its worth the extra 20 mins and $200 fee rather then getting a stop work order.For example, here is a picture of a project nearly 100k for the patio and overhead structure.

My co-worker is looking to sell his rental for what he owes on it....125k.......the property needs about 15-20k worth of work inclusive of a new roof.

I'm currently trying to analyze how well each of these properties performs year to year to see if any are worth selling or in need of some tlc to get them to perform better.

That is because the owners typically contribute thousands of dollars worth a "sweat equity" -mostly site prep and painting.There is a shockingly high demand for short and intermediate term single rooms with bath. 

If you are investing in a different state every couple of years an LLC might be more trouble than it is worth as you'd have to foreign qualify it in every new state you intend to operate in.

Would it be worth hiring a CPA or doing taxes myself?

I doubt someone could determine what my needs are without meeting with me.I do prefer to have referral partners that have specialties that I can refer people with that specific need to them.So, if I know a financial planner does fixed-price financial plans for high net worth individuals and a client asks me about that, they'd get that referral.

That being said, I agree with @Irina Belkofer in that it is not worth the money to have an eviction between you and a family member.

Contracted for 73.5k I wanted it for 50-60k I think the numbers are too tight to be worth it.

I wouldn't normally recommend this, but it's worth the money in this case.Main advice: don't worry too much about it.