Any advice or shared experience would be great.

In order to get there it would be good if you could keep feeding cashflow proceeds back into acquisitions, on top of your continued W2.Speaking from experience, you can manage probably 30-50 units yourself nights and weekends before you really need to hire someone.

Rent control in the bay area can be extreme as many areas have rent control in excess of the state mandated rent controlIn general experience RE investors are not choosing to add a single ADU in single family zoned areas.  

Having no experience is risky.

Sounds like for now the idea of eventually selling the branded account is a no-go, but there still remains pros/cons on each option and I'd love to hear what others have considered or their experience in adding more STRs/boutique hotel type properties to their portfolios.

Most of the lenders I work with (provided you have experience and a credit score over 660) would do up to 85% of the purchase price and up to 100% of the rehab costs, provided this doesn't exceed 75% of the ARV.As for the idea of selling the land, great idea.

You’ve gained valuable experience from your first duplex and are now approaching real estate with a strategic mindset

@Shawn TumaFrom my experience, you can boost rental income and manage mortgage costs by targeting value-add properties and exploring mid-term, short-term, or room-by-room rentals.

To avoid going through the same poor experience, keep reading.Even if someone gives you a referral here, do NOT make the mistake of assuming that the PMC will meet your expectations, just because they met the expectations of the referral source.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

It generally isn't worth the brain damage of experimenting though....especially if you want to move to a new home that you will own inside of the typical lender's seasoning period.