Will banks, who gave me loan on these rental properties or primary home will have any objections, if so, any ideas how to overcome those. 4. 

The problem is if you do not do your homework, you can get stuck in a cheaper property that is in the wrong area and the losses, vacancy and vandalism will be a perpetual loss that will be insurmountable to overcome.  

If the answer is real estate be prepared to put in a lot of sweat equity with long hours (as in any business) and be ready to overcome obstacles on the way.

Im trying to overcome this fear I have read so many books and I want to start taking paths of action.

We would then brainstorm for ideas to help them overcome  those. 

Your being young and having the drive might help your mom to overcome this hardship. 

But you have the "chicken and egg" problem to overcome first: how do you prove you're a "closer" when you can't get the time of day?

It makes a buyer's job harder to have to overcome these unrealistic appraisals.

I do not see the purpose of only allowing close in bookings i.e. 3 months except maybe you can capitalize more on events that have not yet been announced or scheduled, however that can be overcome with dynamic pricing software.

This is another case where education can overcome "fear of the unknown".As for mortgage acceleration, it's really too big a topic to try and fit into a forum post, but here's the "short version":HELOCs aren't borrowed against mortgages, they're borrowed against equity (the value of the property over and above the balance owing on the amortized mortgage loan).