One year after I used that property to pull a HELOC and this year used that money to purchase an off market 4 family property in Clinton for well under market value, which I just recently finished all of the repairs and upgrades on.

I agree that with one property you can just use OTA pricing tools.  5 mins a day for adjusting and you will save money and do it yourself.

At that point we hired an independent appraiser and the numbers came back good and the hard money lender agreed to use them.  

The investor would buy an ugly black box that produced money if it was the right price.

My plan is to take the next six months to try and learn as much as possible about multifamily real estate, while also saving up money to be able to start a career in brokerage.

For me it boils down to more of a personal decision - can I afford two homes, do I want to have two homes and the stress of it, or just take my money out of one and put it in another.

You can attend all the REIAs and read all the books and sign up for all the conferences, and spend all the money, and you are will never really know you can do it until you do.Over 20 years in real estate in various forms and roles, action will beat out intelligence or education or even network 100% of the time.  

I have both, but LTR'S is where I have and still make the most money.

So even if you had a buy out agreement negotiated up front and execute that buy out agreement, the bank would still require him to be guarantor unless something drastic changed on your side financially.The best scenario here would be to purchase and rehab the property using a hard money lender or bridge lender.  

And you spend all that money on updating it will be for not.