If you are concerned about your landscaping you need to hire a lawn service and build that into the rent when it is leased.   

Would you recommend someone who is new to investing manage their property themselves or hire a PM?

You can do well with rentals, far better than mutual funds, but, either have enough money to hire great managers, or do it yourself and expect to work hard.  

Then segment the roles into a "sub-job" the goal is to eventually be able to hire someone else to take on most or all of the responsibilities of each job. 

Look at Thumbtack, I get work off of it and I've used it to hire people with pretty good results.   

I've gotten some really dumb financial advice from money managers, and every time I've hired one I've outperformed him/her w/ the portion of the portfolio I held back to self-manage.    

Should I just hire an inspector/specialist?

I'd hire a real company that does this that has insurance and pays taxes.  

Hire an experienced realtor. 

If both items look to thought out and they are willing to hire a contractor and get a permit, I would consider paying for the materials while they pay for the labor.