I would just recommend only partnering with people that you really trust and make sure that you have legal documents clearly explaining everyone's role, expectations, and contributions (both financial and work wise). 

This may be a wholesale transaction, a duplex, or even a single-family house.Get a trustworthy group of experts together, such as financiers, contractors, attorneys, and real estate brokers.

Hey Andrew, leveraging your existing financial strengths and experience in pooling resources for investment like commercial syndication, you could consider building a diversified real estate portfolio focused on out-of-state single-family homes in growing markets or smaller multi-family units like duplexes or triplexes.

@Lisa GoodingI recommend finding a tax strategist that specializes in real estate taxation and is also a fee-only financial planner.

What subject to invokes is entrepreneurial risk; the thing all real estate investors live with in an attempt to grow our assets, and gain a financial “free” lifestyle.  

this will help with the administrative tasks (e.g. yearly 1099, pay off statements, accounting especially if the borrower pays faster) as well as helping to provide a 3rd party proof of non-payment in case you need to foreclose.Be sure to use an attorney that specializes in Notes, not necessarily a real estate attorney, to draft the paperwork and protect your interests.Good luck.

So, this serves my goal to grow & diversify my portfolio while earning great tax benefits.4) I am in a strong financial position where I could qualify to buy multiple and have adequate reserves to maintain the properties long term and cover any potential negative cash flow during the time I own them.

While the standard Chiacago Association of Realtor's City of Chicago 2023 lease is updated and compliant with new 2023 security deposit rates and local ordinance, we always recommend implimenting an additional "overlay" or addendum that helps protect the landlord against many things that the standard lease cannot standardize that many landlords would like to, like no smoking.

What would you suggest so I can create income and perhaps make a better financial decision for myself.

We have a lakehouse that we're considering listing as an STR part time. Do we need to convert the deed to an LLC first? Do we cancel our homeowners insurance and replace with commercial insurance?