I’m still closing on my first property which, after some non extensive rehab, will let me pull some equity out to pick up more.

For instance, if we had 5 AC units go out, I couldn't cover that on a dime without outstripping my capex and tax savings, but I could probably pay off in a few months.

you add it to the price, and then happily pay it out...That'll happen for sure, in some instances but then that's just like it is now.  

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

The extensive root systems will start caving once removed, which will cause issues for a while -- we had one down in a storm and we're still filling in where roots all over the yard continue decomposing, causing depressions in the yard even 5 years later. 

And of course don't force him into it just to please you (I'm sure you're not)When you verify that he is truly serious about starting the journey, I would 1) have him do an extensive goal-setting plan.

In fact, in some instances even negligence will only lead to a carrier covering legal representation under their reservation of rights and will not cover any settlement or jury award.

Time is running out,  file for an extension, make a payment and get a second and third opinion.  

If it is a partnership/S-corp or a state that won't allow a QJV, then you may want to file an extension & talk to a tax professional who can help you navigate through this as that would introduce a lot more complexity into the mix.