If you paint the WHY to your leadership, I am confident they will let you. 

@Rey Jaj if you’re confident you can rent it in a reasonable time just let them go.

However, with my 1 short term rental I am struggling to remain confident that this is the right strategy as when something does happen it seems I lose at least a couple days with them dispatching and then following up.  

TC: Issue was resolved after 1 day.With these payment, my confidence in TenantCloud has gone down significantly and looking for better solution.

I own a travel agency and have monitored booking calendars similar to our villa for 6+ years, and knew the ROI would be there.

However, being close to the National Park makes typical travel time longer and being closer to the Four Seasons Resort can be accompanied by high HOA fees.

@Justin Ceballos thanks for the great advice, ive traveled for most of the island but honestly the only time im in the north is when i land in san juan.For the most part i stay in the southern part of the island from cabo rojo to humacao.

You want an accountant who can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck.absolutely, yes. we feel confident about filing, but absolutely ignorant to long term tax strategy! 

The bank account verification allows me to accept 1099 workers , business owners, and side income verification with a high level of confidence.

Hi Navid-To start, I am sorry to hear about your father's dementia.It is fortunate that you were able to sell his business and he invested in 6 investment properties in California 10-15 years ago and he and your mother are living on the cash flow from those.You now are thinking about expanding your father's investment real estate portfolio because California is so expensive to live for them but don't have the same experience and confidence being new to investing.This is an honorable goal and you are right to be cautious and thoughtful.You asked about whether you should cash out refinance each house or borrow against all houses to get downpayment for new properties.