(Roeland Park is a high price point area, Which turns into Million dollar homes as you head South into Mission and Fairway.As you head NW, it turns into a C market area.

High to mid 6s depending how much down. 

I tend to avoid looking at them unless a builder is giving a super big rate buy down AND it's not stock.You need to network to find really quality contractors, and then identify a property and buy it slightly beat up & add to it.

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. 

You can try to use depreciation, but there is only so much, you still have to pay the depreciation back (unless you basically die...)You should check out these threads basiclaly about high quality vs cash flowing... 

- 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.