@Simon Asselin what you are looking for is sometimes called "portfolio lending" and sometimes called a "blanket loan". 

Quote from @Brandon Croucier: We have a direct product that does portfolio/blanket loans, even if the properties are out of state .How many properties are in the bundle?

When I have seen this done or done this for clients, the properties being crossed are generally refinanced into the same loan, replacing your first lien (blanket/portfolio loan).

I was still confused when I went online to check my history, but in the end, it did go through and Titan's staff was helpful so I'm not blaming Titan for any wrongdoing.So, overall, I like the bank and all of the people I've interacted with so far (except for the one guy who gives the same blanket response of "speak to your attorney or accountant" no matter what I ask...

Although rare, there are some good wholesalers so it's important not to make absolute, blanket statements.

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It's usually not a lot, but I've had to replace a broken office chair that was only 2 years old, had better quality bed pillows been switched with cheap Walmart ones, and had a blanket go missing. 

My blanket response to you and Jay Hinrichs is that real estate brokers and agents add value.

I run a Real Estate Call Center so I'm always getting asked to recommend skip tracing tools like Lead Sherpa or Share Group.

Without a financial education - it's hard for him to discern which.What he should NOT do is to buy toys or spend it on fun because it'll quickly be gone.If he was financially savvy or versed in real estate - he could even buy a small apartment complex and self manage it if he had some property management skills.Advice should be catered to him specifically though, blanket advice isn't that helpful.