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. 

I would lock in a FIXED rate now, if you can.Obviously, whatever money you pull out and spend on living expenses is money you cannot put to work and invest in real assets.So, using the equation Assets x Return = Lifestyle, you should consider if paying for living expenses now is worth delaying financial independence in the future.Wishing you all the best in your future endeavors.Ken

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?

Our attorney guided us to do an eviction notice with the proper amount of time (30 days, we did 45) to have them leave.