on my last layout i did just that, a raise of 2' in the space of 43' (including R1 curves at the ends)
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but that included restrictions and cheats.
in my (oldfashioned) math that came out at 6% raise on the straights and 3% on the R1 (4ft diam) curves. tested with trial and error, then calculated the working result.
(estimating, that 5ft diameter curves might be good for 3.5% raise)
using 2 axled locos plus motorised tenders (each with additional weight for a total of 2.5 pound per axle) i could draw up either 5 two-axle cars or 4 four-axle cars per train.
downwards there was no problem ;-)
concerning your circle-idea...
a circle of 5ft diam has about
15 foot of track (edited). following my estimation you could gain in that circle
about 6 inches of height (edited).
supposing, that a circle has its end at the same point as its beginning, how would you make/nivelate the crossing needed, to continue the raise?
i would see only one alternative to a straight incline or ramp. that would be to "snake" up the incline. (needing mor length with less raise per foot)
as a fortune teller i would say to you: "i see a lot of trial and error in your future"
have fun!