I was talking to a RE friend.He said it's a bad time to buy* rates are high* homes are expensive in most marketsLooking to hear some counterpoints. 

In 30 years the balloon payment is due to the seller and that's when the taxes are due.Coupling a monetization loan to an installment sale accomplishes the same thing but puts cash in the sellers hands that can be re-invested.

There are many reasons that adding a single ADU in southern CA is a less than ideal RE investment (i will post a list at the end) but the negative initial equity is a primary reason as the initial negative equity position consumes the initial cash flow and can take many years to recover.As for converting your home to a rental….

I have not paid retail for RE in many years and would not in my high cost market (average SFH is ~$1m).  

AS Mike stated its a very cash intensive business.So to me scaling a business in RE does not necessarily mean you own ANY real estate.

I know so many good people in the RE space that I know I should be just fine. 

I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

I am a newbie to RE and just my own personal home and some land.

Small upgrades or re-leasing to market rents could boost your cash flow and provide additional funds for your San Diego purchase.If you'd like, I can connect you with a lender or help you explore potential properties in your preferred areas to see what’s realistic within your budget.

This my friends on BP is just the reality of Real Estate you have two basic methods One mom and pop keep their day jobs and start buying long term hold rentals as they can afford them and if they like it they keep at it..Two you jump in the game and try to make money transactionally IE RE Broker  Flipper Wholesaler MLO  leasing agent etc etc.. this also is a long term ramp.. what the Guru programs attract generally speaking is those that get excited think they can somehow buy a program ( any program pick one) and its going to jump start them to this mythical financial freedom everyone talks about..