This could provide funds for an EMD without needing a personal loan.Bridge loans - While not specifically for EMD, bridge loans are a short-term financing option that can help fund a purchase before you have access to longer-term financing or funds from selling another property4.

Since the home is so new, the title is likely fine but you'll want to make sure you're aware of any liens on it (likely the case if its purchase was financed).An ADU is not a bad idea or even bring in another trailer if the county will let you.

A potential issue I will point out is that I’m pretty sure you need to put into service the property in the year you purchased it, at least for bonus depreciation.  

Hello,I am interested in purchasing a short term rental in the Ludlow, VT market but am struggling to cash flow in my analysis.

Financial freedom requires a passive income that meets three requirements:Your income outpaces inflation: Inflation continually erodes the purchasing power of a fixed amount of money.

Looking to purchase a 3rd home (2nd vacation home but planing to also use it as our 1st STR also).  

I have seen the signs in homes that we have been looking to purchase.

Ryan,From an insurance perspective:1, discuss the claim scenario (Tenant vandalizes the unit) with your agent and see how, potentially, your policy would respond2. require that your Tenants purchase Renters Insurance and have you named on the policy so you receive notice of cancellation. 

Make sure to factor in all expenses, including property taxes, insurance, maintenance, and property management costs.Once you've found a suitable property that meets your criteria, make an offer and move forward with the purchase process.

It actually doesn't matter if you are purchasing for cash or financing - it matters how much the purchase + reno will cost compared to the after repair value.