Hey man!
I think it's situational - Holding vs Selling. If you find a deal that can put you and your lifestyle in a better position but would require selling I'd say go for it. We're in an extremely hot market and inventory is horrendously low. So selling right now likely wouldn't be a bad call if you're looking for the highest price point. However I agree with Dan on his points. If it were me I'd prefer to hold, but as I said it is situational on the potential deal you find. Full disclaimer downtown is does tend to have the longest days on market right now, but thats not saying much since the average overall is 11 days.
I'm house hacking a triplex in IB right now. Picked it up for $1M and after some work we're hoping for a $1.5M re appraisal. Comps put it at $1.35M as is last October, but we'll see! The reason I bring this up is because if you have some extra capital on the side or left over from a sale, finding a house hack that is listed odd or needs just a little bit of work can be huge on returns. (SD relative).
If you're wanting to stay in Little Italy, I have an off market duplex + ADU I can send over so you can evaluate. There are deals to be had in this market still! With how quickly properties are moving an Agent will sometimes miss some details on a listing. Missing/unaccounted for sqft, problems the buyer side doesn't want to solve ect.
Not to reference my triplex to much, but thats what happen to me. Listing agent had a problem with termite inspection. Sellers didn't want to tent because they would have to displace the tenants. So, we took their problem, found the solution, and submitted it with my offer. That due diligence and light rehab may pay off as a 500k equity gain!
I'm ranting, but I'm excited for investors in this market right now. Finding and making Deals isn't boring and feels 10x rewarding when it comes to fruition.
Let me know if you want to check out that off market or talk more details. I also hold REI meet ups once a month in Downtown. Kind of a "speak-easy" right now so hit me up if you want location details.
