Hey @Ryan Marble, it is something that you can do no problem, like the others have said.Regarding figuring out your return, take some time and look at all the listings that would be similar to what you are planning on AirBNB and VRBO.Look at their nightly rates, occupancy and amenities.

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. 

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

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

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.

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.

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.

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.

For example, a city could be currently zoned Agriculture, but if the city has this area planned/expected to be MF by 2030, your chance for rezoning is much more favorable. 

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