Eventually, I’d like to expand to other types of properties and markets, but I think getting that first property will build the momentum and spark the fire to keep going, instead of being stuck in perpetual analysis paralysis.A bit about me - I’m a software engineer by profession but deep down, I don’t have a true passion for tech so I would want to eventually transition out and focus on real estate full time (of course, this will be much later down the line).With these crazy COVID times, it’s hard to get out and actually attend meetups and get to know people in person, so I’d like to connect and get to know some other folks local to the SD area and even beyond!

You pose an interesting consideration, at what point is just getting into a deal a worth while action even though it has impaired performance vs sitting the sidelines and perpetually waiting.

Further, the "buckets" for passive losses offsetting passive gains don't really matter a ton nor does a stepped-up basis at death as part of estate planning from perpetual tax-deferred wealth creation if 99 percent of one's ability to generate wealth relates to mixing their labor with capital in entrepreneurial pursuits. 

This one of the perpetual questions in real estate - I have built decent cash flow in this property, so now it's worth quite a bit more.

My goal is to break the chain of lower-middle class living that my family has so blissfully perpetuated through multiple generations. 

Document the space once and use it in perpetuity unless there is a significant change to the unit or building. 

No matter how hot the market, appreciation cannot outpace inflation perpetually.

She is a person who would rather buy her dream house (imagine stereotypical millennial design aesthetics)  a little farther away from the city instead of a BRRRR in a C class neighborhood.

More brand new military need to be thinking that way, not going out and buying a (insert stereotypical boot vehicle purchase).

(and this is not offend or stereotype anyone).