Your Financial Goals are as simple as generating two very basic sets of number...dollars really:1)  Make enough Profit (lump sum returns) to Pay Off your personal debt...ALL of it.2)  Get enough CashFlow to "cover" your monthly bills...ALL of them...and to replace your current method of doing so.The overall Plan, is comprised of a series of Measureable Milestones made up of groups  of the individual Financial Goals (Debt Payoff, Cash Flow)...all lined up in a row.  

But I think an actual check as a gift would be odd and crossing the line between professional and personal.The reason I'd opt for a nominal gift is because landlording is a "people" business and getting married is a major milestone in someone's life.   

Pay for project total, and in milestone payments.

Pay in increments of 10% upon mobilization and then 20% milestones until you reach a punchlist and the last 10% upon completion.  

A Payment Schedule should outline Payment Milestones, Amounts & Terms which describe the work that needs to be completed in order for the Contractor to get paid, how much the Contractor gets paid, and when the Contractor gets paid.Form W-9You will need to get a W-9 from the Contractor so you have the Contractor's Name, Address & Taxpayer Identification number which will be used for preparing Vendor 1099s for your Contractors at tax time.Proof of InsuranceBefore hiring a Contractor you need to make sure that the Contractor is carrying the proper insurance to protect your property, investments & personal assets.

I am looking for something more strategic to were I can set targets, milestones for projects, properties, and my company and track and manage their progress.

I always paid for all my materials out of pocket, and then paid the contractor in pre-arranged increments to be paid when certain milestones are hit.

Did you have a scope of work contract including schedules, milestones, and payments? 

GOAL: we surpass the milestone and target of 10k$ a month net passive income —so we can FIRE, we currently working are in active duty military family and stationed in the panhandle of Florida.

Do the harder stuff and lay out a project for the customer with regards to how the milestones will go, where the QC checks will be, and when payments will be issued, based on project costs (materials, and labor).