I recommend paying and hiring a Realtor and RE Attorney to walk you through your first few transactions.The best leads are the ones you go out and get yourself.

Hire/Find a local and experienced Team that will help do things when you call.  

I hired a foundation expert and had him look at it, can't remember the exact amount, I guess it was around 500$, the guy actually paid very little attention to the foundation, he was looking for the gaps between ceiling and walls, cracks around windows / frame, and drop in floor level, in the end he said it'll last another 100 years.

- Hire a personal assistant to manage the reservation and manage a cleaning service I would need to identify Is it too risky/complicated?

My purpose is two-fold: 1) to help me keep organized and have a reference manual that I can look back on, add to and tweak as needed 2) provide instructions for every task that I could possibly outsource/hire out down the road so that I can scale and grow my business.Any stories, tips or advice you can provide would be greatly appreciated.  

It's a new area for us, so we hired a company based on a referral from our agent.

I don't hire contractors who drive Porsches.

If I hire a contractor to fix it, it will costs $2k-$6k.

If you try to hire people in The Valley you're probably going to be paying at least 2X what you'd pay in other tech hubs in other states.  

If you do not want to physically look at a property hire someone like a freelance photographer on task rabbit or craigslist or go to http://www.wegolook.com.