1)
Yes it can. It's slightly different here; chloroalkanes are reacting with a hydroxide ion, while the reaction between ethanol and hydrogen bromide is forming water. The hydroxide ion is less stable than the chloride ion as can be seen by their base strengths, so it will latch onto the carbon more readily than the chloride ion. However, in the reaction between ethanol and HBr, the alcohol group is protonated by the acidic hydrogen in HBr to form a R-OH2 + group, in which the water can drop off favourably for the bromide ion to bond to the carbon. Hydroxide ions do not appear anywhere here.
The first reaction is conducted in basic solution. The second reaction is conduced in neutral or acidic solution. They are not direct opposites of each other.
2) When phosphoric acid is deprotonated, it bears a negative charge. To become deprotonated again, you're asking for a negative charge to lose another positive charge. That is inherently energetically unfavourable.