Even if your most expensive formal eviction was only $1,600, the real cost is in the time.In Connecticut, the eviction process can easily take 3–6 months (or longer if the tenant contests), during which:You’re losing monthly rent — potentially $4,000–$8,000 or more.The tenant may stop maintaining the unit or cause damage.You’re likely paying legal fees, court costs, and potentially storage/removal fees after they leave.So while cash for keys feels like a “bonus” to the tenant, it’s often the cheapest and fastest path to getting your unit back in rentable condition — especially in states with long and tenant-friendly eviction processes. 

OOS investing isn't the easiest thing to do but is a great way to get your portfolio started if investing locally isn't feasible for you. 

For example, as you are well aware and a master of Henry, in mini storage if you look at a deal that was rent stabilized in 9 mnths and another in 24+, that's 2 very different deals and market indicators that require one to dig deeper into the why.

The STR was never fully utilized and their is some room to raise slip rates and increase winter storage.

User error & storage, like I've mentioned several times.  

The showings will eventually lead to applications, so long as you're priced right.Splitting the unit will come down to cost and feasibility.

My lease makes very clear the yard is not a storage area. 

If that's not a feasible option then out of state might be a good substitute.

Goal is to move on from W-2 as soon as feasible and set up my children for wealth in the future.

The goal is to make the most of house hacking while it's still feasible for the family, then shift into more permanent plays as things settle.