I'm not sure, but I've heard this consistently from other investors.

Luckily I have an attached gazebo with simple baseboard heat - lol that and the outdoor pool are the two places the temp is consistent.    

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).  

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

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!

Does anyone have a suggestion for an in-person (Denver) or virtual meetup/group/class/etc that could help me establish some consistency and accountability (and hopefully networking) with real estate investing? 

Maybe bag groceries at the local store.When I started, title plants consisted of large books known as tract books where documents were indexed geographically with the entries made by hand by people known as posters.