There was no arguing, no confrontation, no problems. 2.

Hi guys,Happy to provide some feedback, and I hope I don't come across as confrontational.

I confronted them and the excuses started.

Whenever I confront my tenants about this, they either claim it's being taken care of by a third party payment plan they set up (probably some sort of debt consolidation program, presumably) or they tell me they have taken care of it. 

I’m a young woman in my mid-20s, and my tenants are middle-aged men, so I’m nervous about confrontation.

When confronted with this, the OP chose to provide a convoluted reason as to why this risk was somehow less risky than providing specific collateral.  

There was no arguing, no confrontation, no problems. 2.

However, our STR permit was just approved.Tourism is a little slower in the winter being a beach community so we are now confronted with the decision to stay with the LTR plan for consistent income over the winter or furnish and list it as a STR over the winter and into peak season next summer.LTR Pro and Con:Consistent income over the winterWill be tricky finding a tenant for a short winter rental being unfurnished.

Pride definitely plays a big role, and unfortunately, I’ve seen homeowners choose to “lose big” rather than confront the situation early.That’s why having open conversations and offering clear, judgment-free guidance as early as possible is so important.

You don't want "yes men" you want someone who will push you a bit on things you say and be ok with you questioning them.You will need to be confrontational and be willing to tell them you don't understand where they are coming up with their results and they need to prove it to you.