After years and years of being frustrated by how tough it is to find honest, communicative contractors, I decided to start a Handyman/contracting business.This is NOT a solicitation.My question is – What are Property Managers / STR Owners / Investors looking for when they need a handyman and how are they finding them?

Give some examples of the Italy issues.  

I’ve often seen this happen where initial approval is given, but debt-to-income issues arise once they discover you’re purchasing another property.

Quote from @Jaycee Greene: Hi @Chloe Salcedo, welcome to the BP Forum and I'm sorry to hear about your medical issues!

The real issue you should address up front is what does the seller want?

If you made those free they'd be complaining about jobs or supermarket deserts or lack of public transportation or some other issue.

Cash offers are often particularly appealing to sellers because they eliminate the uncertainties that come with financing, such as loan approval or appraisal issues.

Getting them all I same room however would be an issue.  

Based on a quick answer from Perplexity it seems like there would be no issue with you buying the home and collecting passive income, but you may not be allowed to manage it yourself since that is considered active work.

do you have issues with the city if there are cars parked on the street or lawn?