There is a fenced in front yard with over grown grass that hasn't been trimmed so it does not have much curb appeal. 

Looks like it has some good curb appeal. 

Maybe its the rookie in me, but heading into this phase of the real estate cycle with a bunch of cash to play with seems really appealing. 

Re-envisioned the basement space to make more usable, and invested in upgrades that made the house more appealing and liveable, while disciplining myself to not spend on the little things that weren't going to really add value.

Any advice as the ROI doesn't look appealing.

A benefit would be that we could paint the brick and generally improve curb appeal of both sides.

Is there another way to put the proposal together to make the 10 year option more appealing to them other than decreasing the rent$/sf?

If you want to appeal to a larger audience then you should take into account the cost of hard money in the holding costs and bake that into your offer.

Having gone through the process of buying my first house made me realize that ot wasnt as hard as i thought and now im very interested in investing part time to get to the point that i can start doing art again on a full time basis but not have to rely on it as my full income, which odly enough helps the creative process and helps me get better deals on the art i sell because im not desperate for the money.So I have been doing a lot of research, and it seems like flipping single family homes sounds appealing with the end game of buying some small multifamily homes for a more steady passive income.

You better have strong argument, why they shouldn't raise or should lower, ready for appeal time.