His payment jumped up to an amount he couldn’t afford, so he stopped paying.

I want to avoid falling into a mindset of thinking we can't afford to invest because of the needs in front of us.

Assuming you have 5 units, each worth 300K, and you could afford the loss of one, but not all.

In a city like Philly, you will face many challenges - you need to learn the market and know the neighborhood and the block and make sure all of your numbers are within reason, you need very reliable contractors, you need a to understand the permit process, you need to be familiar with market expectations. 

About me, most of my assets are RE but in another market so I would be diversifying in that market.Potential for appreciation is very uncertain: prices have risen a lot locally lately and are as high as they have ever been, and it’s unlikely higher prices would be affordable by locals.

Part of the investment thesis was getting it for a bargain, then building an ADU complex on it as affordably as possible, getting it to cash flow, and realizing value on both the rental income but also property appreciation given the work going into it.If the property will really only be worth ~$1.70M once we are finished, I will likely just stop the project now and exit the house as soon as possible.If you do not get dollar for dollar for projects such as this, how would house flipping ever work?

Plus, compared to other parts of Florida, the Panhandle is still relatively affordable, making it a great option for first-time investors or those looking to diversify their portfolio.Another huge perk is Florida’s no state income tax and landlord-friendly laws, which make it easier to manage and profit from rental properties.

These platforms are affordable and offer comprehensive reports (credit, background, eviction history) without you having to handle sensitive information directly.Verify Employment and Landlord History: Your plan to request pay stubs and a landlord reference is solid.

When you build enough capital/assets/net worth to afford a reasonable monthly cushion you can see if the lifestyle of a full time investor is something you’d want to pursue.  

Not sure how common or widespread that is, but it has happened.