In all my years of Property Management in one of the most tenant friendly Cities in the World, I bet there will be a lot of interested people, regardless if they are actually planning on buying in a tenant friendly City.My management style would be considered highly unusual as I approach these issues so that it becomes a win-win situation and take into account the human element of the tenant.There is potential for me to add more to that Podcast to include how the Portfolio did over the 28 years growth period (1998 to 2025) with real numbers.There will be things like making the Portfolio safer as I age by paying off the Mortgages and increasing cash flow, etc.I'm also a Cloud Software developer (Salesforce specifically) and will be employing a lot of A.I. in 2025.The RE Portfolio is cash flowing very well and I can afford to integrate experimental A.I. to test it out.Things like A.I.

That said, the right team on your side can make the permitting process and inspections far less painful.I’m curious... as you refine your plans, how do you see yourself balancing the home’s original character with these modern upgrades, and which element of the design do you think will win over the pickiest buyers? 

Combine this with the deliberate targeting of unsophisticated investors or those without the resources to run ordinary diligence and you have a winning recipe.

Even in the off-season - you can optimize visibility by setting competitive pricing, using high-quality photos, and enabling Instant Book with flexible policies.For older listings, try adjusting prices with dynamic tools, highlighting upgrades, and regularly updating your title, photos, or descriptions to stay fresh in search results.These tweaks can make a big difference!

I see it from a guest's POV if they booked a place and show up to something that looks shabby, then instantly you are starting off on the wrong foot.

So the Janitor usually wins, defined as making more passive income than your expenses, because his expenses start off so low and stay low.Unfortunately, after you play it a while, you get to know what to look for, like when that one stock becomes available for, I forget, $3 or something ...

Would this be an optimal win-win for risk reduction + tenant satisfaction? 

It seems like a win-win: tenants benefit financially, and landlords strengthen tenant relationships while making their properties more appealing. 

You probably don't need much to win.

Example - if you buy in the original auction and win at 12%, you accrue 1% per month.