Just wanted to thank everyone again for the help.I can't say I fully understand all the issues raised, but it sounds like the bottom line is that there is no way to move the asset out of the s-corp without triggering a capital gain liability.Interestingly, the thinking required by me to address your comments made me realize that I am not depreciating this asset. 

If you didn't claim it in the year the property was placed in service, you can elect to claim it in a subsequent year, as long as the property meets the requirements for bonus depreciation in that year.

It is also my understanding that many lenders still require a personal guarantee for properties held in an LLC.

We have an apartment complex in a state where we are required to have tenants sign Window Guard forms and for the first time in decades, a tenant asked about getting window guards.  

Sounds like it was probably a reverse mortgage, and the balance owing is higher than the property is worth.

In the residential world, some requirements are relaxed comparing to commercial so it's up to you whether you want to spend the money to have a better planning versus skip the planning and perform the work impromptu.

A well-located / well-appointed property can get $1000+ ADR at 70% occupancy on an annual basis.Deep pockets required though, property prices are high. 

You should gain more appreciation, so it’s all a fine balance & you have to weight each and see what’s best for you. 

I've personally worked with a handful of "investor-friendly" lenders, primarily on DSCR loans in recent years, and each time I've run into significant delays, lack of transparency about the process, have been fed the requirements in a piecemeal fashion (every few days there's a new random request rather than having it all organized from the start), and have even run into lenders who were substantially misinformed about the real estate industry or the laws that govern it on both a local and federal level.I think there should be a better site to encourage accountability by tracking how long it actually takes each lender to close their loans on average, and what unexpected hurdles investors encounter when trying to work with them.I can't seem to find such a site.

If you're doing a risky flip, the return requirements will be higher.