It’s still a worthy strategy to force cash flow that’s rare to find in SoCal, especially if you can reduce the cost of construction by doing a conversion/using an ADU grant or even buying a property with an existing ADU In general, even if the ADU valuation matches your cost including grants, they are usually not worth it in southern CA in single family zones. 

Would encouraging longer stays realistically help reduce this, especially for a medium-sized cabin?

That is a 3.4% cash on cash return in year one (7903/232000)Year 2, reduce 7903 by 5592 because there won't be property tax break so that is $2311, or 1% c/c return in year 2 (2311/232k)Year 3, reduce the $2311 by $4930 for PM fees for a net loss of -$2619 per year or a -1.1% c/c return in year 3 (-2619/232000)Essentially, these numbers are so far off of pro forma and there is pretty much zero wiggle room on these numbers. 

The BEST method for real estate investing is very simple: increase earnings, reduce expenditures, save, and invest from your own funds.You should focus on increasing earnings and learning how to manage your budget.

Organizational Delays: Section 8 offices are often overworked and understaffed, leading to slow processing times for new tenants, delayed rent increase approvals, and poor responsiveness.Benefits of Section 8:1.Long-Term Tenants: When you get a good tenant, they usually stay for a long time because of the tedious process required to qualify for Section 8 housing.2.Consistent Income: If Section 8 covers most or all of the rent, you typically receive reliable monthly payments, reducing the risk of non-payment (as long as there isn’t a large tenant portion).3.Lower Barrier to Entry: Because properties in these areas are often more affordable, it’s a good way for new investors to break into real estate without needing a large amount of capital.Overall, I’ve seen the good and the bad of this strategy.

I have great tenants but my property taxes have increased significantly so my net cash flow each month is reduced.

Remember that the leveraged purchases are not going to add significant cash flow immediately and borrowing against existing properties will also reduce their cash flow.

Especially as it relates to being able to rollover IRAs and old 401k money into a Solo401k.Self employment allows you to contribute large amounts to Solo401k to reduce FICA taxes.

When it comes to analyzing properties, I’ve developed a specific checklist to make sure the home fits both resident needs and operational goals:Square Footage: Ideally, at least 2,000 sq. ft. to ensure enough living space for residents and staff.No Stairs or Pools: It reduces liability and keeps the home accessible for everyone (this is just my preference).Corner Lots: I love corner lots because they often provide extra parking and outdoor space—both of which are critical for families and visitors.

., retirees, dual-income households, or tenants relocating for work) may reduce risk.Stay Up to Date on Landlord-Tenant Laws: Understanding your rights and obligations can help you navigate issues more effectively if they arise.That said, if the potential risks are keeping you up at night and the financial pressure of an eviction would be too much, selling may still be the best option for peace of mind.