Because from this, it will direct what strategies and market to look into, which to ignore, and the base parameters to start putting together a PLAN. 

It might be possible if the hours towards the 1099 work apply towards one of real estate related tasks that qualify for real estate professional status.The issue with a W-2 and doing the tasks is that you are not an above '5% owner' so the hours wouldn't count. the 1099 might be a workaround.

Which company should I use for direct mailing?

I also needed to start applying for schools for my kids and could not wait long to find a amazing deal. 3.

Without being callous you should certainly reach the point where two main rules apply 1) it's your way or the highway - your system or no system and 2) you provide a service and thus will be compensated for your time regardless of what outcome the owner is trying to achieve.

Can anyone point us in the direction of learning materials for beginners?

As far as your credit goes, you can apply to several lenders and have them pull your credit, the bureaus look at that as comparison shopping for mortgage rates and they will hit your credit, but for much shorter term.

If anyone who runs a successful flip (5+ a month) or LTR (50+ units) has time to chat I would appreciate the direction and reassurance.

The back end isn't great, but the key is to become a partner which unlocks a lot of great features as well as a personal representative with a direct phone number.You also need a good PMS that auto-charges credit cards and integrates with the booking.com API.

You could try contacting them directly.