All of that culminates to high 20% occupancy; up to mid-30s - if you are on water or if you are nearby skiing (<10min).

Wow yes I feel like I'm hearing first-hand how wrong it could go, but I have a few questions and concerns if my standards will follow suit of the unlucky investors:-For sure I would want to work with Class A or B rentals (I had a property 5 min from my home and the tenant was HORRIBLE, so a reliable renter is CRUCIAL), but not sure if my price range would find such a tenant.

For your $2M property, a cost segregation study estimates $316K in first-year depreciation (compared to $28K with standard straight-line), potentially saving ~$117K in taxes at a 37% rate.

I could likely see many things from the TCJA being made permanent, mostly procedural items like the higher standard deduction and child tax credit (Plus eliminating exemptions).

The standard process is already long enough, add on the scope of things and that's some significant time.

Multiple asks muddy the waters and make people feel as if you are nickel and diming them which you are.   

We dug a little deeper and found out the city had a timeline to expand water and sewer services within 18 months.

Simple standard sales process."

Water - landlord plays in JC heights typically.

I haven't reviewed the Standard Lease Agreement yet, but all I need is the right to sublet, and possibly some negotiated capital responsibilities (owner pays for repairs over a certain amount or split responsibilities on certain expenses).