I attempted to do a cash out refi into my LLC, and was told all i needed was to add my mother as a minority member to my LLC to properly transfer the deed.   

Now we’re buying a second property to use as an STR, and I’m afraid we’re going to have a huge mess at tax time if we don’t get proper guidance.

Short Term Rentals are great but it takes a significant amount of upfront work and cost to execute them properly. 

Take ownership of your mistake and learn to do the proper due diligence recommended above😊

Make sure the “guts” of the toilets are working properly.

The one set of tenants did not even bat an eye (had not had a rent increase in 7+ years prior), and the other set appreciated it and moved out about 2 months after the rent increase (with proper notice). 

HOWEVER, if you already knew about a pre-existing roach issue and maybe failed to disclose it to them properly/didn't set correct expectations when they moved in, then it's on you. 

You have the winning hand here.As a landlord you have to not react to the "I have an attorney." 

Proper transparent accounting is essential to any partnership, including when partnership is family.

[2] Rather than demo the garage, why not just install a 2nd proper septic system.[3] This guy must have some kind of car collection--what's his daily driver--some kind of "Far Out" Hot Rod?