@Jordan Turner A lot of these questions should are best answered by your realtor and lender as they are the experts that should be guiding you through the process. In the meantime, maybe this will clear it up a little:
1. It's up to you if you want to use the home inspector provided by your realtor. If you trusted him/her enough to help you locate a property, then I would think you could trust him enough to provide an inspector. If you trust the seasoned investor you talked to more and he recommended you a specific inspector, than go with that one.
2. Great contractors can be hard to find but they are out there - there are many resources on this site that give great advice on selecting a contractor. My recommendation is to reach out to contractors who have been used by people in your network already, that way you know you will get a legit reference.
3. There are likely two different types of escrow accounts that you will have when you purchase this rental property. The first escrow account (the "middle man" that the investor was talking about) is set up when you purchase your house, and it holds funds that are used to pay your property taxes and homeowners insurance. The lender sets this up, and you should definitely reach out to him (the loan officer assigned to you) so that he can explain it to you, I'm sure it's something that he does all the time. Basically, each month, you make a payment for your mortgage, taxes, and insurance. The portion of that payment that goes towards the taxes and insurance in put in an escrow account, which is controlled by whoever is servicing your debt, i.e. the lender. Once a year, when your taxes and insurance are due, the lender pays it from the escrow account. The amount in this escrow account doesn't really matter much to you - the key thing to understand is the amount that you owe each month in taxes and insurance.
The second type of escrow account you are talking about is completely different. This is an account that you can set up and control when you get tenants in the property, and you collect security deposits from the tenants. The seasoned investor was telling you that your bank likely will allow you to open a separate account where you can hold the security deposit funds from your tenants, until they need to be returned to the tenant when the tenant moves out.
Hope that helps - talk to your realtor and lender though, they will answer these questions much better than I can and more specific to your situation.