Starting problems/damage to engine

Ive been experiencing a lot of trouble getting my slant to start, My question is could I be causing damage to the engine by cranking to much, Ive had a lot of short cranking spurts to check spark etc. Gas not being a great lubricant worries me as Ive never had to try this many times to start.
The question should be - Why is so hard to start - fix that issue and you will fix the gas in the oil issue.
Start with the basics.