@Leeling Chew we require anyone over the age of 18 to fill out an application for the property even if they plan to just be an occupant. 

You'll get a feel for the age of the neighborhoods, the vitality of the commercial buildings, the ease of location, the closeness to jobs.The markets you're describing are more linear, and usually have lower capital appreciation.

I understand that at my age, focusing on properties with strong equity growth potential (even if cash flow isn't immediate) is a solid strategy.

I feel like in today’s day in age there are so many tools for STR operations and I cannot believe there is no integration for a merchant of sale transaction or some kind of financial app/ software that can take the remitted taxes and pay them to the government automatically.

I'm unsure if it's the entire EU, but forsure in Italy, they receive a pension at a certain age.

Depending on the actual age of the property, at least some level of deferred maintenance is not uncommon.

Quote from @Travis Smith: Age 56 and retiring from farming and I’ve been very good at avoiding income taxes with depreciation and business expenses.  

Directly withdrawing funds from a Traditional IRA before the age of 59½ typically results in taxes and penalties.However, one option to consider is using a self-directed IRA.

Second link is a similar size, albeit 10 year older home, in Setagaya Ward (a very desirable neighborhood), but still "only $1.2M. https://www.homes.co.jp/kodate...https://www.homes.co.jp/kodate...(2) Age. 

I helped an Invester from the age 14-19.