I rented out 2 of the 4 rooms which allowed me to bring in more than the cost of the mortgage.

I just received the following response from TurboTax regarding adding the study:TurboTax online does not allow the capability to override any certain transactions, ie; depreciation.

I would take him up on it since you have absolutely no risk.Unless you sign some sort of non-compete and are not allowed to do deals outside the partnership until he recoups $500k then that would be a large potential issue.Good luck!

As long  as the current zoning allows 4 units, it should qualify. 

Before diving in, make sure your mortgage allows for owner-occupied multi-unit properties, understand local regulations, screen tenants carefully, financially plan for potential costs, and have a clear exit strategy for managing the property in the future.

I have done 2 successful flips and also have one 1 buy and hold.Now that I have a little skin in the game I’d like to ask my dad who is 62, with a 6 figure 401k to allow me to use $50,000 to invest in more real estate.

Most states don’t allow you to charge for any work you do, so hire people.

The other option would be a bridge loan that allows you to pull out the cash to buy the other home and the bridge is set up on an interest only rate until the home sells so its more affordable.   

For example,, if the house was worth $200k and the lender needed a 75% loan-to-value, they would only allow for $150k financing on the house. 

If you plan to live in this property for as long as you own it, then it might not be a bad deal because it will allow you to live in a good area and a desireable school district and you'll be able to offset the expensive mortgage cost with rent that you get from your tenant.