I shifted focus but def plan on going back to the strategy and ultimately plan on graduating to deeds so I can acquire the land. 

I run a small private real estate investment club and we love to plan happy hours for visitors to Milwaukee.

How feasible is this plan from the POV of a seasoned investor?

Planning to self-manage remotely / family in town close by in case of immediate action.

You could add a clause in the lease stating the penalty for late payment.I like the idea of electronic locks.I would identify the items that need updating and plan accordingly; roof, furnace, etc.

This will allow you to acquire more rental units and also being able to use the vacated unit rents at 75% to help your debt to income ratio DTI.There is a FHA 100 mile rule if you do plan on using FHA on your 2nd house hack.

I understand there is no “right” way to do it but my plan was to get hard money for the purchase of the property and use a heloc for the renovations.

I don't have 2 years of work history, but I do plan to work a W2 job until I start seeing progress in my rental estate journey.

My plan has been to use 1031 and build my equity until I own a farm w no morgage and it cash flows. 

Work on a payment plan, but have it such that the entire cost of the damages are paid in full before the lease ends.