Once they drop to below our required lead flow to rent out the units when we want we'll drop it by $25. 

Most if not all of these properties require SIGNIFICANT cap ex rehabs and conventional financing won't touch them; you'd likely need to go the hard money route at 10-12%, 2 points, 12-18mon turn around.

These special assessment were thousands of dollars, and there was no sufficient reserves from the monthly fees to cover these large biggers, so the owner were required to cover the shortfalls out of pocket, what a great way to ruin your cash flow and ROI.There are benifits to condos, including tennis courts, playground, swimming pools, club houses, and fitness facilities. 

I have the funds to buy another primary residence in this area but not enough for an investment property that would require 20-25%.

Fix and Flips require Money(and or atleast reputation).If you are in a bad financial situation, fix and flips may not be possible for you(especially if you have no experience).

It does take 1-2 weeks to accomplish, so does require some effort and monitoring on your part, but sounds like you are a diligent self-money manager, so should be easy for you to accomplish. 

Some areas allow commercially zoned properties to share one large septic system (think sandmound or gravel type system) or would they require an individual on-lot septic? 

I recently completed one on a multifamily property and found it to be a cost-effective approach.That said, there are a couple of additional factors to consider beyond the code differences between a garage conversion and new construction:Coastal Overlay Zones – If your property is in a coastal overlay, building a ground-up ADU may require Coastal Commission review, which can add time and complexity to the process.

Success in real estate requires courage, perseverance, and the willingness to take calculated risks.Internalize these principles and apply them in your real estate endeavors, and you will be on your path to success.

Maintenance and potential repairs will also require a long-term financial plan and setting aside a contingency fund for such expenses.The steady cash flow, appreciation over time, and tax benefits can make a meaningful difference to your wealth in the long term, especially with the principal paydown on the mortgage.However, if managing the property from a distance feels too burdensome, or if you’d prefer the certainty and flexibility that comes with having less debt (especially given the high mortgage rates), selling and using the $100,000 in equity to reduce your loan for your next home may be the smarter move.