I'd make sure you can get financing (eg are approved for that amount) and then if you're willing to take the risk of not being able to pull all of the money out that you expected and the numbers still work, then try it.

I would say the best thing to do if your looking to save money and make as little mistakes as possible is get one for the first property and is willing to grow with you.

The property is nice enough and in a good enough location that I would be comfortable living there for that amount of time, but I am ultimately looking to make money on this deal. 

Analyze this with him and then 2) have him start bringing you properties that he has run numbers on, in a serious spreadsheet, have him sell you like he was your partner.When you think he's ready and has saved at least some money for a DP, help him get started with a little loan/gift.

I had 1 rental property in the past, thought this would be the starter rental to my portfolio ended up being a money pit and drove me away from real estate investing. 

As a PML, I generally like to have all my money plus a high interest within 6 months.

Using private money to pay off the deed then looking into equity loans to rehab and purchase other properties.

There is one that I really like that has gone through multiple cycles with no investor money lost.

Plus why have an account for paying down bad debt....the money should be going to paying the bad debt, not sitting in a bank account.

You will then have a few options with that rent money....you can put it into principal or you can start saving it to purchase yet another property.