Matt, my understanding was that suction side cleaners are better for smaller pools and pressure side cleaners for larger pools, is there any truth to that? There is also the Polaris 360 pressure side cleaner that doesn't require a booster pump, but I don't know how well that works. There are also more energy efficient booster pumps like the Polaris PB4SQ and Hayward 6060 which would reduce running costs. I'm not advocating for anything in particular, but the OP has a few options he could explore if he decides against using a robot.
I was coerced into buying a robot. I bought a Dolphin s30i.
I don't care for it because:
1. The cord tangles horribly - so much so that it formed permanent kinks.
Pool Store said it should not, and they replaced the cord right before the two year warranty went out.
Interesting note - It had not be used for maybe even half of that 2 year period.
Another interesting note - new cord also started kinking almost immediately. So either the cord doesn't have enough strength, or the swivel has too much resistance.
Friend told me - you have to take it out every day and let the cord sit out in the sun to straighten it and remove the kinky memory.
a. That doesn't help
b. I don't want to take it out every day. I want to set the schedule and leave it alone.
2. I don't like the cleanup. They tell you look - just open the trap door - everything falls out in your trash can - bs
You have to remove it - empty it - and then clean the inner filter and outer filter with a hose - not pleasant in the winter months.
3. I have never felt like it cleans like my Old Antique Kreepy Krawly.
If there is stuff on the bottom, and you watch the s30i - it just drives itself around.
If the pool is in the same condition and you watch the Kreepy - It leaves a White Stipe everywhere it goes.
The hose never kinks, and the in line strainer holds many times more debris than the robot. In the Fall, it packs leaves in tight.
So now I run my s30i when the pool is in decent shape, if it ever gets bad, or when the leaves start to fall, I always go back to my wall mounted suction side Kreepy Krawly.
I even bought a new Kreepy one time - it didn't last a year - luckily I still had my old style. I went back to that and that is what I use today.
Maintenance consists of mostly Foot Pads and Skirts - it's basically maintenance free.
I may have put a couple of bearings in it over 15 years - Oh yea, and (1) Flapper - the only moving part.
I changed to the Flat Skirt from the Pleated years ago - seems to last much longer.
And to answer your question - I have a 30k gallon Pool, so it's not small - If I woke up tomorrow and had a pool twice that size, I'd just go buy more hose.