Try $65/sq ft for first estimate and use Standard Plans from AASHTO and the DOT for details and examples. Any changes from these assumptions will require a higher fee.
Wrapping the column with either high modulus fabric, (with epoxy matrix) or steel is a normal method of retrofitting for seismic requirements. This may work for you if bending is the critical fail mechanism.
If the design optimum moisture is held in the native soil and the compaction of the bedding/spring line is uniform and meets compaction requirements then the pipe will utilize the available wall strength. The backfill is equally important with thin lifts compacted at optimum moisture content...
If the holes are excavated immediately prior to concrete placement then a minimum strength of 80% of F'c is recommended before disturbing the adjacent soil. Using high early mix designs, this can be less than 24 hours.
High moment foundations such as light poles do not use grout, but bear on leveling nuts. Grout is unnecessary when the bolts/plates are correctly designed to accept the load.
A heated form for the concrete mix can get you 50-75% of the ultimate strength in the first 18 hours. Try a 8400 psi or better design mix warmed to 160 degree max(f) at 20 degree/hour increase from the initial set temperature.
Calculate the horizontal forces on the structure, (wind, waves, seismic), and apply to the proposed foundation. The 1000 pound per square foot design may not match a saturated subgrade, (a better than 90% chance that the soil is sufficient), but expansive or collapsing soils should be checked...
Expansion joints are unnecessary. Either the water will maintain a close temperature or the steel will be stressed within the allowable limits for changes of temperature.
The net compression due to bending will be reduced from the uniform tension. A conservative method would ignore this lessening for the compression side. The tension would have to be permanent and unchanging to use the lesser compression.
Speed will NOT effect the "braking load", the coefficient of friction between the tires /pavement is the limiting case for locking the brakes and causing horizontal load.
Cast in place drilled piles/caissons will work if the horizontal subgrade modulus can be determined. Wind foundations are moment controlled, (a vertical beam with horizontal load).
Steel resting on the surface before topping is the surest method of knowing the vertical location for that steel. A low/medium frequency compressed air driven vibrator made out of a series of closely spaced pipes will assure good consolidation when used on leveled/placed mix. A chair would be...
The maximum moment from the jib crane can be resisted by the caisson depending on the horizontal soil modulus and the depth. I would model the caisson as a rigid structure with a pivot location approximately a third up from the bottom of the caisson. This is usually the most economical design...