I am currently in the market to purchase a tri-plex with the plan to live in one unit, make upgrades, and rent the other two out.

The electrical panel is original, so an upgrade might be needed in the future. 

Seems like you may need to upgrade the rigs or something kind of fun. 

•Likely, the new property wouldn’t be cashflow positive due to the market conditions.2.Upgrade to a Bigger Property and Sell•Sell our current home and move into a larger house to better meet our family’s needs.• Use some equity from the sale to make this transition smoother.I’m torn between maintaining our current home as an asset and buying  a new smaller house to use as a rental after we move back in versus simplifying and focusing on a single upgraded property Considering factors like market trends, potential equity growth, and quality of life, which path do you think would be most beneficial?

For example, if local regulations require energy-efficient upgrades, prioritize these changes to avoid fines and demonstrate your commitment to sustainable practices.Case Study: In 2020, many cities introduced rent control measures.

As we have all seen, Californians are leaving in droves over the past couple of years, and fleeing to Florida, Texas and yep...Arizona.As long as we continue to stay under LAs housing market for affordability, we are going to continue to net those homeowners wanting an upgrade to a bigger house or lot. 

My father is a certified contractor in NJ—he’s built one home, flipped four, and consistently handles upgrades and maintenance for me and his other clients.I’d appreciate any tips or stories from those who’ve turned equity into a profitable venture.

It's likely you'll be able to raise the rent as well with the upgraded unit and you can look to market it during the time of rehab. 

These properties will have very few or no upgraded amenities, and rents will be below market.

(This option would most likely add debt by pulling a loan against property 1 to payoff and do some upgrades to property 2, and all credit cards)Best, GeoffScott Trench made a spreadsheet for exactly this scenario!