Does anyone have any experience / can advise on the process in each of these counties?

I have some single family rentals north of you in Delray, happy to share my experiences if you want! 

As for taxes, I'd recommend connecting with a CPA or tax attorney who has experience with rental properties held in LLCs.

If so, what has your experience been? 

It sounds like you are already getting great experience in STR management!

It may be beneficial to consult with a local real estate agent who can provide insight into current market trends and investment opportunities in both Connecticut and New Jersey.

@Kaycie GunnIf you want debt financing hard money or private money lenders will fund with typically 25% down paymentIf you are looking to syndicate and raise money from investors then that is a different animal and you will need to file an sec exemption to raise money and depending on your experience it could be moderately challenging to near impossible.

There are some situations where a well-seasoned investor can borrow 100% of the purchase price and come out smelling like a rose, but only because they have the experience and they can absorb the loss if they screw up.Increase earnings.

I’m new to this so wondering how you all with experience would handle a situation like this.

But I have seen and heard some really funky stories so I’m here to see what experiences others may have had.