If Planning does determine the existence of your ground floor unit, it will require you to legalize the unit through the existing Planning code process assuming zoning supports the third unit OR using the new ADU program making your fast track condo conversion a passing dream.With regards, to some of your latter comments and questions:1) Any un-permitted work (including corrections) is not a good idea as a quick compliant from a neighbor can bring an inspector knocking on your door with a NOV especially in the current environment where everyone is SIP.2) Legalizing existing constructed spaces can be hit and miss based on the inspector you get.

There are additional trees leaning heavily toward my other neighbors house and possibly could hit my house. 

Dopamine hits.

I've received different advice - on one extreme is sell off all your rentals, take the cash and take the capital gains tax hit and invest in stocks/index funds (not from a RE investor, from people I know who are horrified that I have more than one mortgage), which I won't do.

We went from making an average of $7.3k per deal in 2017 to $35k per deal in 2019, sometimes hitting home runs of $70k, $80k, and $90k in profits—more often than we could have imagined.We also started building a team, hiring Acquisition Managers to meet with distressed seller leads.

Filter properties by geography and “rental yield” and get alerts when new inventory that meets your criteria hits the market.Let us know about any feedback you have and expect iterations on this in the back half of the year and into 2025!

If the property is bleeding money every year from repairs, maintenance, or turn over you'll never get ahead.You can tap equity with a HELOC (challenging right now), cash-out refinance into a new loan (much higher rates), 1031 exchange, or sell (tax hit) but the numbers and property condition need to guide this decision.

Most stuff in CHS that's worth buying is gone in pocket listings or shortly after hitting the MLS.

In terms of the loan(s), I currently have a steady and competitive W2 job and very low DTI, however I’ll ensure to verify the rules and regulations for rental income when shopping lenders, so I don’t hit a roadblock when buying the next rental. 

It was hit on in a few comments but you have to look at the overall risk of the property.