In my area we have a gentleman who will look at an investment property for you, tell you what needs to be fixed, produce a scope of work - everything you'd want to know How much money/percentage% should I have saved up before starting this journey?

I feel like this could be better to watch over the work the contractors are producing too.

I find it difficult to buy 1% producers in my market unless its an off-market value add belly to belly with a motivated seller. 

It will take longer to find that multi family deal that will produce the income you need to house hack.

The Closing Date on the property should be tied to a point in time that has the property and project you envision fully entitled in a manner that will allow for the development and operation of the project AND when you have secured 100% of the debt and equity capital needed to develop your project.Your 3rd priority should be using the time provided in the purchase contract (from mutual execution of the contract to closing) to conduct all of the due diligence activities cited in the critical path and any others you may encounter during the DD process.After Closing, your 4th priority should be to develop the horizontal improvements (roads & utilities) to produce finished lots and to then sell the lots to 3rd parties and use those funds to cover all or part of the cost to build "your dream project".If you are interested in taking on Priority 1 (critical path and budget) DM me and I will send you an Xcel worksheet that can get you started.

Wouldn’t we want all of our properties to produce cash flow?

If I'm reading this correctly, your friend produced the 20% downpayment and you took the burden of the loan?

higher LTV equates to higher leverage which can produce higher ROI. you have to live somewhere.  

I enjoy the opportunity to buy many products and produce from the network of local farmers.

Meaning, you live in one of the income producing units.