This would help us benchmark and explore simpler alternatives while understanding how complex the structure mentioned above truly is.I assume they are not actively managing their business?

Having a cashflow breakeven property with a loss for tax purposes can have some tax benefits that you should consider exploring. ...

If you discover one that sounds potentially relevant, and you have not explored it - see if you can still get hold of your accountant to ask.

The goal is to create cash flow, do some value add work, and be able to take advantage of the STR loophole to help with my W2 income (hence the self managing).I’ve been exploring towns like Beacon, Woodstock, Hudson, Newburgh, Lake Hopatcong, Highland Lakes, and others.

The property sits on 5 acres, and after a successful first year with cash flow, I’m exploring ways to expand.Initially, I considered building another home on the property to use as a second STR.

It’s always exciting to explore other booming markets and see what makes them stand out.Happy to connect and chat more about this!

Have you identified a property yet, or are you still exploring options?

Probably wiser to deploy just a bit more ($1.2 mm - $1.3 mm) and try and get a 3 or 4 unit property via FHA.Jersey City is very hot right now and certainly worth exploring, but have you also considered Brooklyn, Queens or the Bronx? 

.• How to think creatively about building wealth.Once at the property, the kids explored, asked questions, and saw firsthand how opportunities are created through smart investing.Involving children in real estate teaches them:• Financial literacy in a hands-on way.• Entrepreneurial thinking and problem-solving skills.• The confidence to believe they can achieve financial independence.It’s amazing how small moments like these can inspire the next generation to think bigger and dream bolder.How are you involving your family in your real estate journey?

Always formalize the agreement in writing to define costs, profits, and contingencies clearly.Let me know if you need help structuring the deal or exploring funding options.Best,Drago