I hate walking away from a deal once I’ve put my mind to it.  

Jessie Vasquez is one who comes to mind.

Note these cannot be with stocks, as the passive activity is what matters here.

STRs can vary significantly & we've found that it takes about ~3 years of STR activity to optimize income with repeat guests, online visibility/activity, etc.My recommendation is to go with strategy two to live where you want and find a way to get into the rental game another way with a partner or another way. 

Much appreciated if you still have a company or two in mind.

be mindful of the limitations of section 280A.I think your goal with having a STR in your personal residence is to not have the cash-flow be taxable.However, it would be hard to have the losses offset other forms of income such as W-2, Interest, Dividends, regardless of how active you are.Best of luck to you in your search.

Basically my question is does a lender actively monitor things like taxes and insurance after the loan has closed to make sure it still fits their standards?

Mind if I pick your brain?

I would first start by deciding how you want to get involved - actively or passively.

Community engagement is a cornerstone of life in New Braunfels, with residents actively participating in local initiatives, events, and neighborhood activities.