Your new potential guests are insurance companies for homeowner displacement (flood, fire), buyers looking to move to the area but not sure where they want to be, sellers who want to sell but have nowhere to go, contract workers in the area, adjunct professors on a semester job, etc.

It might not need a full replacement if it's still doing its job—keeping the rain out and protecting the structure.

Research markets, consider factors like job growth, population trends, and property prices.

In the next 1-2 yrs I'd like to move out to either a bigger place or a new new city (job related relocation etc).

Even though I have a great corporate sales job with a W2 income over $200k annually, I've always known I didn’t want to rely on that income forever.

Or plan to get into a House Hack when you graduate and half a good-paying job.

The text/chatbot can also do the same.We looked into this because our best appointment setter left for a more stable corporate job, and the other one got promoted within the company.

Those are two completely different jobs, but it illustrates the same premise. 

I do enjoy my day job and hope to stay there as long as possible, with the hope of peeling off by 45 (just turned 40 this month) and after that would consider maybe using the cash flow to benefit me a bit. 

The owner built a 1 bed apartment in the basement nearly 30 years ago and did pretty a nice job.