Would it be an issue if I was self-performing a majority of the work myself?

How bad you get to screw someone has limits.To stay away from such issues, investors need to justify their actions, in valuations and in charges for services performed, justifying fair and equitable dealing.

I have been researching and growing my knowledge in various aspects of real estate for the past 8-10 months, but no cash to perform.

That should get the attention of someone high up to get some heads rolling.if it doesn't I would send another letter so the same higher up stating the actions you will take that will be billed back (plus any administrative surcharge) to the tenant for not performing per the lease.  

I am only going to do this 2nd job for 3 years and I know the first year is going to consist of getting out of the toxic debt so that leaves 2 years of either paying off rentals or investing heavily into ira and 401k...

. #4 mentioned by Brian, in any option contract there cannot be any requirement of the optionee to perform anything, it cannot be contingent on any type of performance.In this case, a commercial lease allowing sub-letting, the tenant may have maintenance responsibilities.

The key is to keep it consistant with former trade lines.

Those early years I mentioned, they consisted of time spent seeking conventional financing as well as any landlord who may consider 'seller financing' to two brothers still wet behind the ears.

Did you perform landlord duties?

If you invest in your kitchen you will attract renters quicker and more consistently than if you invest in another bedroom..