Some/many lenders don't like a 2nd mortgage behind their first (like the skin in the game), however there are both bridge or permanent financing options out there allowing you to leverage anywhere from 90% CLTV - 100% CLTV, but don't expect good terms...

The Long term, after some reserves, I'd like to bring down the assessment costs since I worry that this will negatively impact the property value. 

Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

When somebody asks for advice, I always try to put myself in their shoes and understand who they are and what their objectives are so I tried to do that with you with the little amount of info I could garner from your profile.

Now, in 2024, we're seeing $4,000 per month just on the main unit and $1,800 on the other unit of the duplex.Long story short, it's a long term play.

I think this will be the short term realization, and anyone that did not wait on the sidelines and jumped in with the intention of a short-term re-fi might have to tap out. 

That's my biggest concern.But I should also look at the tax and long term benefits.

Looking for guidance on the best way to proceed going forward in terms of asset protection and how to structure all of this real estate… 

The East Rock area of New Haven (near Yale) is a huge outlier in terms of pricing, very expensive. 

Since I am entering this field in the latter part of my life (63), I do not want 'long-term' investments as I am not interested in making millions, but having enough for the remainder of my life to 'Vive La Vida Loca'!