Mortar, paint & bonding materials deteriorate leaving cracks, gaps, etc. which can be concerning to look at, but this is very often addressed with repointing.

Its market driven.

I'm very interested in finding a property in the Algarve region or possibly another tourist driven area for STR and eventually living there more and more over the next 3-4 years. 

The appraised equity rarely materializes on a sale in these markets but the appraisals offer false impressions of the "asset" that was acquired.

But, I am not willing to commit to 50 years (if I am lucky) of never harvesting material equity from my rental properties at this time so that she can inherit potentially millions or tens of millions of 2074 dollars at stepped up basis.I plan to pay the tax man and spend some of my money at some point.

I recently used it to generate custom images for my STR coaching Powerpoint material. 

This property would be for my in-laws to purchase and move into, but I'd ideally dovetail any success into finding investment properties as well.So far, I've driven around the neighborhoods my in-laws would ideally purchase and jotted down the addresses of the homes that clearly need some TLC.

Yes, you personally aren't living there, but with high crime comes unqualified tenants and high maintenance costs (stolen materials, broken windows, etc.).

Keep in mind local zoning laws and market conditions in Portland versus Salem—Portland might offer higher rents but stricter regulations, while Salem could provide better cash flow opportunities.Your design approach has proven successful, so continue focusing on appealing upgrades like kitchens and bathrooms, but prioritize cost-effective and durable materials for rentals.

Great marketing material on.