An appraiser will not look at NOI or cap rates, and many residential appraisers may not know what do with those #'s anyway. but they will look at the GRM's (gross rent multipliers). 

Rehab consisted of complete gut renovation of kitchen/dining area, new hardwood floors and refreshed bathrooms (new vanity and paint).I am bullish about the long-term appreciation prospects of the property and have trouble envisioning the hold strategy over the next 10-15 years. 

The city is one that’s consistently listed as a top 10 2024 real estate market, the projected cash flow is intriguing ($50,000 - 25% down payment, estimated $7500 annual cash flow), both units are leased until October and December (as a potential new landlord this gives me some security), but I feel hesitant with offering on a century old property.

You would get more value add and more consistent temps.

For the long hold, San Diego I likely to have the better cash flow potential (assuming you do not consistently extract cash out of the properties).  

Too many mortgages into retirement means your multiplying your risk and headaches for what a tiny cashflow?. 

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

I track all of our requests in our markets so that I can come up with a multiplier between LTR and MTR rates.

Then, multiply that number by how many hours per month you're spending on bookkeeping.

Vacasa ranked us the top place to buy a beach property last year & we consistently hit most of the top lists for affordability & revenue potential!