(Either with the roofing company, a heloc, or a personal loan.)Either way you will probably be way ahead on interest saved unless you have a sub 6% interest rate.

Be sure to shop around for the best terms and understand the refinancing process post-rehab to ensure your numbers work.

My recommendation is to see if you can work for a company in real estate or wholesaling that way you get training and education while getting paid 

@Sarah HartsteinThe way you spoke so highly of your success embodies what investing is all about.The more I research investors who are successfully investing outside the country, the more I feel inclined to shift my goals toward international real estate investments rather than focusing solely on opportunities within the U.S.I will most certainly keep you in mind once I am ready to expand my portfolio! 

Option 1: Lower Down, Higher Rate (10-15 Year Term)For the Seller: Steady cash flow, better return than banks/CDs, avoids capital gains hit all at once.For You (Buyer): Lower upfront cash, keeps more liquidity for operations, long-term financing stability.Offer Price: $2.2M (Full Asking Price)Down Payment: $220,000 (10%)Loan Amount: $1,980,000Interest Rate: 8% FixedAmortization: 25 YearsTerm: 10-15 Years (Negotiable)Monthly Payment: ~$14,846 (P&I on 25-year am.)Why It Works for the Seller:They get a consistent $14,846/month income instead of a lump sum that could trigger taxes.8% return is way better than typical bank investments.Avoids broker fees (~$100K savings).No property management headaches—just collects checks.

Are there particular types of properties or investment scenarios where private lending works best?

If it's something you want long-term it may be best to get the real deal but it's been cost effective for me to offer without the big commitment. 

Are there any potential flaws in the way we are setting this up?

Wish you the best of luck along the way and great to see so many of you interested in Southwest Florida! 

$300-$400k will likely not get you even a 2-family in the best area of New Haven unless it needs a lot of work, but will get you a property in a top flight area of Hartford.