After a side lining injury.

Without bigger pockets I’d still be sitting on the sidelines with no clue.

Fixer upper and got me off the sidelines How did you find this deal and how did you negotiate it?

I think I will pass on this deal or at least stay on the sidelines and see what he does in the long run (perhaps reoffer at a later time with a lower price if he can't seem to sell it)@Jaysen Medhurst thank you as well for your help and for following up to clarify your original post.  

Now, I'm at a point that I'm tired of watching others grow successful businesses/investments while I sit on the sidelines, afraid to use my hard earned money to do the same! 

I don't invest in appreciation per se either.I understand why you got the objection of "we're on top of the market so I will wait in the sidelines".Here's how I overcome that objection.

I sat on the sidelines for too long.

Take action, dont sit on the side line.  

OR, I'd find a deal and calculate it but it would push my DTI so high that it might put me on the investing sidelines for the next few years.

I've considered simply buying properties with that cash and avoiding financing all together, but I'm afraid that will lead to a significant portion of my cash "sitting on the sidelines" more often than it's being put to use.