RentingFamilyMember is not interetsed in making money, just not paying the food, utilities, etc. of the SiblingRenter.(2) RentingFamilyMember's AGI is too high and Schedule E passive losses are limited.

You don't HAVE to buy points, but if you have a high DTI, the lender might not be able to do the deal unless you do, we can't tell from the information that you've provided here. 

Most of the houses we are finding on the MLS are priced too high for the numbers to work on a fix/flip. 

- You missed utilities in your holding costs- For your first rehab you should plan on a little more than 6 months, just in case- You might want to double check your tax number as taxes in NY can be pretty high- The biggest area where mistakes are made for new investors when it comes to flips and BRRRRs are in the ARV and the rehab cost.

You just have to ensure that the mortgage balance is not higher than your offer; otherwise, the seller would have to come up with money to close, which is highly unlikely.

As for doing work yourself, you are a high paid SW engineer.  

Due to the high costs in San Diego and current interest rates, I would most likely only be able to put up to 10% down.

Also, I would highly suggest that you go in person with your application to the Municipal Building in Center City, it will take over 5 weeks if you mail it through snail mail.

We are already a fortunately high net worth family. however, that is from my spouses W2 income, so at this stage we don’t really have anything tangible to “leave behind” and we want to try to build generational wealth for our child. 

The electrical I am in the process of lowering all the outlets to the same level since 2 of them are about 4' high.