No, taking out a HELOC and spending it does not reduce your taxable capital gain when selling your home.

I currently have about $50k in cash and am looking to spend no more than $250k on my first property (less depending on the area, number of units, etc.), inclusive of any renovation costs. 

If you are building on your own existing lot, you are sacrificing privacy for sure, but if you are comfortable with that in this stage of your life its a good way to maximize what you already have than trying to go to market and spending over $1M on a decent duplex. 

This allows the Board to spend the funds on anything, and if they do, the owners would need to restock the reserves!

Sounds like we are in the same boat with a handyman :) And to @Jonathan Klemm point, I have to weigh the mental capacity of handling issues remote versus spending time with family.

The few times I called the office, they were always happy to spend time talking. 

Where I have seen AI or other tools help is with the initial data entry process, so one can spend their time analyzing and modeling the data (vs. keying in data).

We only work with investors who take the steps to get pre-qualified and spend a bit of time getting to know our company and allowing us to get to know them. 

That is dissapointing that they did not vet the people they would be spending hours and hours touring properties.

Monitor your spending habits to make sure you’re consistently putting money aside for both the short-term and long-term costs of real estate.