Chris, you can always start out with the common questions like: what investments do you own, any interesting projects you've completed recently, what investments are you working on right now and what is your investing model (flipper, wholesaler, etc...).

Not all companies will write a Homeowners policy in an LLC name (although that is becoming less common). 

Any insight or "what would you do" scenarios is helpful!

@Troy S.I have some cash, a shitload of drive, 6 years of construction management experience with a top GC, a year of sales experience with a top Equipment Rental Company, a RE license in MA, a few residential deals under my belt and common sense.

Probably depends on your strategy and how well any of those scenarios fit into it. 

You would both be tenants in common and if one of you dies your share should go to that surviving spouse.

No legal advice given... confirm how this fits with the instant scenario.

Your dilemma is common, and fed by the fact that the Solo 401(k) is often over-hyped. 

- Does anyone use a specific application/lease only for these scenarios?

We did a total renovation - New TPO roof, New Windows, New Plumbing, New Electrical, New Base Board Heat, New Window Units, LVP flooring in the common area, Sanded and Painted Hardwood floors in the units, New Kitchens and bath for each unit.