I'm a big believer in roller trailers with a Powerwinch because you don't need to dunk the springs and axles, so bearing and spring problems are virtually unheard of. The single axle EZ Loader 4000 lb capacity trailer I bought new in 1985 still has the original 5000 lb capacity axle and springs on it! The rear cross member does get wet and I did replace it last year. I'm running 22575R15 tires on 15" galvanized 6-lug wheels; tires are load rated at 2830 lbs @ 80 psi, but I've towed the boat all over Florida with them at 65 psi with no problems. I can launch at any ramp at any tide level and could even unload my boat on the grass in front yard if I had to!
I used to have roller guides on it but found that I didn't need 'em once I got the rollers adjusted correctly so I removed them. Your trailer looks similar to mine, so I assume it's set up with cross members that pivot so the entire rack of rollers can tilt as the boat rolls off the trailer. There is so little friction in the roller system I have to use the clutch on the winch to keep it from coming off the trailer too fast! (Because of this, you need to have a strap or chain securing boat's towing eye to the trailer; Don't depend on the Powerwinch clutch to keep boat on trailer!)
John, here's what I'd suggest you do to your trailer:
1. Add a couple of keel rollers to rear cross member to keep boat centered as it comes on the trailer, as shown in first pic below. Had to add the roller on front of X-member because it tilts enough that bottom of hull can scrape of front of X-member if I only used one roller!
2. Put a 2x4 under hull and use a bottle jack on frame of trailer to lift one side of boat at a time. Spread the rollers on each rack as far apart as possible.
3. Move each rack of rollers outboard until the outer rollers are outboard of the outer step. If boat isn't currently centered you'll have to compensate for that, but the racks want to be equidistant from CL of trailer. As the boat comes up on the trailer, the keel rollers will keep it centered until the aft most rollers go over the edge of the step; once they engage that step, the boat will come on the trailer perfectly centered every time, regardless of cross winds or cross currents. I've been launching and retrieving my boat this way single handed for about 10 years and it works perfectly every time.
4. I back the trailer in until the tires are wet, but no need to get the rims wet. This puts the aft keel roller just about an inch or so below the bow eye. I ran a length of SS leader from Powerwinch switch to corner of trailer so I can run winch until it takes up slack in winch cable. I run the winch off truck battery until it starts pulling boat, then I start engine so all the winch current comes from alternator instead of battery. (Note pulley on winch hook with double line in last pic for extra pulling power! It's a little slow but steep ramps are no problem!) I also chock all 4 wheels with 4x4 blocks when retrieving! I discovered that when boat is first coming on trailer, it can lift back wheels of truck up on to the chocks, causing them to slide on a slick ramp, but if front wheels are chocked, it can't do that!
One other thing to check is to make sure that boat isn't heeled to one side when in water. My roller system has so many degrees of freedom in it that if boat isn't level in the water to begin with, it will tend to come on the trailer sitting the same way! Adjusting the rollers correctly seems to have eliminated this problem however. Also if you install an old Ford starter solenoid on your Powerwinch so that all the current goes thru the solenoid instead of the switch, your switch will last a lot longer!
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