@Stephen CuccI would develop around San Diego.

I’d like to develop a tiny house/small house on it, ideally, but I’m not sure if it’s a good investment for the long term.

In short, 2 heads are better than 1 and you can split tasks, combine assets, and tackle larger projects because you are building a team.

If the sites are larger than 1/2 acre (NOT AN EXACT NUMBER), and you are needing to develop the land (i.e. roads, utilities, mass grading) I would then recommend involving a civil engineer on a site plan and to do a more in-depth due-diligence. 

We have a custom-developed software program that prints the custom letter and label.

It is quite a daunting task ahead, but nothing I’m not more then capable of excelling at.

The building inspector and I have developed a relationship of respect for each other. 

If you're going to rehab, make sure you develop a sequential plan, don't just start in.

If you're in software development, you're good at what you do, and you're not focused on some bespoke in-house developed platform that no one outside of your organization has ever heard of - Austin will be a better job market for you than Philly. 

From there, a fixer-upper house-hack or live in flip might be a great opportunity to develop some practical skills that can help you supplement your income or add a lot of value economically to your purchase!