(Available time, money, income, family situation, credit availability, time horizon, real estate market location and phase, medical situation, etc etc.)

Location?

@Landon Sheveland  don't think your renovations will overcome a bad location. 

Otherwise its all about the classic location location location.

Would it generally be a location that tends to have a higher cost of living? 

one truism I think for rental real estate is returns and price points are very much risk adjusted highest returns lowest price points  biggest risk.. smaller cap or return and prime location least risk..

Here’s how they approached it:1.Scraping Listings: They used web scraping tools like Beautiful Soup and GPT APIs to scan Airbnb for properties in their target areas.2.Image Analysis: They trained an AI model to analyse listing photos, identifying homes with solid potential (good structure, layout, location) that were undervalued due to low-quality photos.

The townhouse is located in Aspen’s sought-after lodging district, where STRs are fully permitted.

I like Dundalk because of it's location (easy to get south and 20 minutes away from shopping areas.Any advice on this area?

We are selling one property in a location that has permits and other restrictions it would take Sherlock Holmes to find and when you inadvertently hit one there are fines plus the permits and delays.