It seems a great HVAC guy is really hard to find and worth his weight in gold in Florida. 

My dream has always been to live in puerto rico and have a place here in NY.

It was a dream purchase for me and my wife, but after joining Bigger Pockets and all the great folks on here helped my move into the STR game.We ended up with a standard 2nd home mortgage that was almost immediately transferred so we just started listing it on VRBO and AirBNB.

Think, I have FULL WEIGHT of liability on my shoulders for ANYTHING my agent's do.

She repeatedly said how much she'd always dreamed of being a homeowner. 

It's true you get a tax deduction for your mortgage, but you also pay taxes on whatever else you decide to do with that money.I would list all of your known investment opportunities, what you think the after tax returns would be, and a risk level 1-5.If paying the mortgage is a clear standout on that list on a risk/reward basis, I would spread out the $60k over a period of time and apply it to principal.You might have other goals like cashflow or reducing risk which might weight towards paydown also.

. $400 for a 2-day rental of an 11-yard dumpster might seem high, but it’s important to consider what’s included (delivery, pickup, disposal fees) and whether there are any weight limits.Alternative Options:Bagster Bags: These are large, disposable bags that you fill with debris and arrange for pickup.Junk Removal Services: Some companies specialize in hauling away specific types of debris.

Not saying you shouldn't invest in real estate, you totally should, but if you can find your dream job doing something that you love while also investing in real estate, you'll be setting yourself up to be wealthy but also have a purpose in life.

would have to get a quote from an excavation company . depends on what the materials are for weight 

You have one of those dream situations of using other people's money.