@Jonathan LudizacaFrom a lender's perspective, starting in 1-4 units gives you experience and many more lenders will be open to first time flippers in this space versus multifamily. 

You’re absolutely right about the market potentially shifting, and this is where those who are ready to act and think creatively win big.

From a tool perspective, nothing should be set it and forget it.  

It has a lot going for it from a long-term rental/cash on cash return perspective, but I’m not too sure about short term rental demand and occupancy.

Keep in mind if there are economic shifts that you are seeing, so is everyone else, so you may have missed the boat.   

It’s also worth diving into local regulations and HOA rules—they can shift quickly in coastal markets like this.

I might also compare it to other markets..like Austin or Phoenix..where property prices have been shifting (from what i read in CNBC) but still show growth potential.

I have shifted gears on my plan- I purchased a LTR (A Triplex) in Rochester, NY. 

It keeps things professional while giving you room to grow your expertise.I admire your perspective on keeping your parents’ resources separate from your own—it’s smart to want to succeed on your own terms.

Quote from @Amit Chugh: While searching for apartments, i noticed a commercial apartment listed as Section 8 property, does it make any difference from buyer/seller perspective when it's listed as section 8 property.