I typed in variations of "rent increase, proposed legislation for 2024 for San Francisco" in Google and don't see anything saying a landlord can't increase a property to market rent on a new tenant after the previous tenant moves out.I talked to 2 PM companies in S.F. and they both said I could rent out a SFH at market rate rent if my current tenant moves out (family member who is getting a deal).

Selling your property to a buyer what would an ideal ad say to you?

Therefore trying to get a bit creative with the financing.Positive cash flow will almost be impossible (as I'll have to probably take one bed away, and then build a bath and a kitchen) in what I've been finding, so Im trying to offset the mortgage as much as possible.Long term, ideally I get to keep it and the 2nd unit adds to the cash flow if I ever dont need it anymore. 

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.

Does anyone have any quickbooks alternatives that work for class tracking and or can recommend an accountant (ideally in the San Diego area) that would be able to get us going in the right direction?  

What type of housing? 

The tax treatment of replacing HVAC systems depends on various factors, including the type of property (residential or commercial), the cost of the systems, and whether they qualify for immediate expensing or need to be depreciated over time.For residential properties, the cost of replacing HVAC systems is typically considered a capital improvement rather than a repair.

He mentioned to me that I should liquidate most of my assets so that I could qualify for loans such as FHA and similar types since those are more for lower income earners.

In my market, these types of changes don't happen in a vacuum. 

from your qn , you seem to be looking for infill type projects ?