He has been saving his money for years and has plenty of money saved but no experience with real estate investing.

Almost nobody in the Upper Peninsula has air conditioning though so maybe can save money on just doing a new furnace and not a full HVAC, we'll see.  

The quick short answer in my opinion is this: If you want growth stick to the small multis that you know and once the mortgages are paid off retire fully.

@Franklin PerezGetting your real estate license can be a smart move if you want MLS access, networking opportunities, and savings on commissions, but it comes with costs and disclosure requirements.

Consulting a tax professional now can help structure ownership and financing efficiently, ensuring you take full advantage of deductions, depreciation, and potential tax-saving strategies like 1031 exchanges in the future.This post does not create a CPA-Client relationship.

Doing it in December will not save you any taxes anyway.

My original plan was to save up for a year and buy my first home.

@Roman StefaniwWhen retirement accounts in the US get financing, the loans are called "non-recourse."

This would reduce my monthly expense to $3,568, saving $144/month.Questions for the Community:Which of these options do you think makes the most sense for a long-term rental in NYC?

This will save you time and effort, as you won’t have to travel long distances to manage different properties or handle tenant issues.For your first investment, I suggest starting with 2-4 unit properties.