I suggested to Clint to stack some credit cards to have zero rate for 12 -18 months as his cushion for cash.

I bought my first home paying 20k over asking price with a 10k appraisal gap, but lucked out with a good interest rate (3.9%) this was in 2022. 

I purchased a property where there was a verbal lease, month-to-month, 0 security deposit, and the rent was 1/2 of the market rate... some instances you're better off having the seller evict 1st.

On the surface, it seems like it meets a lot of broad criteria for being a positive investment, including a positive cash flow at a currently high interest rate, but I don't want to miss on my first step into this.

Are people still investing is San Diego or have the high interest rates and low cash flow moved investors to other markets?

I've got at 2.29% rate on the current primary and a mortgage payment all in of about $2600.

Obviously, you don't want to have a high interest rate locked in, but if it is the only way to close on an otherwise good deal, the short term cost may be worth it.

You should probably place more equity in this deal and refi once rates drop or sell it if you can't take the cashflow losses.

It's worth considering the credit rating of an insurance company and how long they've been in business. 

Three years ago, my wife and I purchased a duplex with a 3.25% interest rate.