I see folks get into crazy deals not knowing what things will cost, so good on you for having that skill set and being able to fix everything!

They focus on deals in the gentrifying areas of town, and target higher end tenant base they have built through professional networks. 

I specialize in basement egress window installation but I am just as skilled in whole house remodeling. 

Now I’m not worried because o have automated online systems for rent collection, contractors and licensed repair professionals on speed dial, and I have some boots on the ground in the form of family who can lend their knowledge and keep an eye out for me.My first thought to this question is : if I’m worried that it may be too far ,then for me it may be too far.I could never do a flip that far away, IMO.

Other things you can use to demonstrate your intent would be your normal practice, rental agreements or rental listings, written correspondence with your professionals etc.You've got a pretty healthy gain to shelter for sure. 

First, tell you boss at your company and make sure it's okay -- it doesn't do any good to make an investor mentor if you also lose your 9-to-5.As for approaching the individual: 1) explain why you're interested; 2) say that you did get the ok from your company, and that you're doing it in a totally private not-related-to-your-company way; and 3) offer to help out with his properties like you said.A key thing to be clear about -- if you offer to do any of your professional day-job work for him on the side as a favor for him helping you out, you need to be sure that your company doesn't mind you doing it.

What skills for you have?

Attorney is the best practice professional to help establish buy-sell agreements and other exit strategies, including provisions in your partnership agreements.

I didn't account for property management, as I'm fairly confident in my organizational skills, free time and availability that I can handle that at least for a small, first unit.

Everything I am doing though I am learning new skills and I can apply them moving forward.