Timing the market rarely works and if it does it's usually about 95% luck and 5% skill.

I discovered like-minded investors that had the skills and time to do the work, and I brought the funding. 

It was that skill and trust in that function why many persons placed 7 figure sums into his hands happily and readily.

People want to partner with people they like and trust in addition to all the hard skills-it looks like you are pretty good with numbers.

Start with listening to the podcasts, identify what you are good at, could be finding distressed properties, analysis, or phone skills, etc.

Pay him and use him or don't in the future, but if you don't get multiple quotes, you only have one dollar figure to make the decision.Like @Linda Weygant said, you're paying for the skill, not necessarily the time. 

He has experience In running a business which is what he’s doing now and I’m a skilled tradesman.

I typically underwrite deals in the $10-$60 million range which has improved my Argus skill IMMENSELY.

I have online experience and was hoping to figure out a way to leverage that skill to decrease the time to a regular income.

He runs a family business and I’m a skilled tradesman and we each have 1 rental property at the moment.