I would not factor the tax benefits and appreciation from acquiring the property because I would look at them just as a bonus. 

Perhaps you're thinking of bonus depreciation which is still 100% this year. 

Congrats - starting small and having a learning experience is the way to go, nice profits/return a bonus!

Bonus question:  If I do the bare minimum to get the property habitable and list it for rent, will that technically count as "putting it into service" so that I can then do some additional "qualified improvement property/personal property?" 

Ive heard of the concept of bonus depreciation and cost segregation and was wondering if anyone can elaborate more on this. 

Views are a really nice bonus. 

I also use this for a week or two during the summer which is a nice bonus. 

If the area warrants an alarm, having them in, in the first place is a bonus/selling point for tenants..

Since it would seem that the 2 units are "in operation," you would depreciate the reno or take the available bonus depreciation deduction.Usually, its not advisable to hold your residence in a LLC. 

We will renovate the fix up the first floor additional dwelling and plan to rent it out as a STR for the rest of 1st year to maximize the return of our renovation expense against our W2 taxes via the Cost Seg / Bonus Depreciation.