The U.S. typically withholds 15% of the sale price if the property is sold by a foreign investor, which can be reclaimed later based on the actual tax liability.Cross-Border Transactions: There are specific reporting requirements and compliance rules for moving money between Canada and the U.S., so make sure you're familiar with those to avoid any issues.It sounds like you're on the right path, and with the proper guidance, you'll be well-prepared to make your first purchase.

Since your Boston condo is in an LLC, transferring the title to your personal name to satisfy the lender could potentially trigger tax issues or disqualify the exchange. 

I would say local property management company is ideal so you learn the legal compliancy, too, BUT we also have many virtual non-local employees that are amazing at their job and have learned a lot in property management even if it's not in the state they live and own their own rental property in. 

 I’ll also add that there are some instances where just making additional payments to pay down principle could trigger the due in full clause.

I'm looking for advice on how to feel more comfortable pulling the trigger on my first out of state rental property.

Compliance and RegulationsAlthough it takes careful preparation and research, investing in the US from Canada may be a lucrative endeavor.

I have "Rental Property Investing" sitting in my cart but was waiting to pull the trigger until I added a few more things.

I was also told by my cpa that transferring the property from the LLC to our personal names will trigger a tax event.

I just have to pull the trigger and then work to get my books in order.Appreciate it!

Most HML are using a large LOC that dictates their underwriting criteria they dont have the ability to change that criteria lest they be out of compliance with their money source..