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.

Look at the graph in the link to show the radical change over time.   

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.

Put Chicago on that graph!

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.