Things that have stood out so far in my research: 1-Close proximity to Metro North (90 minute ride to NYC)2-Vassar Medical Center3-Marist & Vassar Colleges 4- The Walkway over the Hudson5-Restaurants/Cafes/Hotels, etc.Thanks for your time.

If willing to invest more effort for higher ROI, consider Option 3 (building your own team), though it requires time to establish reliable management.

There are occasionally opportunities for grandfathering if there is evidence of legally established conversions that were done previously, but no permit records exist to show it was done. 

That project taught him that buyers in these well-established neighborhoods pay close attention to the details..things like making sure the ceiling lines are clean, storage is intuitive, and every inch feels purposeful rather than tacked on.For your project, thinking about the functionality of the added space is key.

$300K is a lot of credit card debt and probably didn't happen overnight (unless it is medical bills). 

Through connections with people in various markets, I was able to establish short-term rentals internationally, manage properties in different states, and diversify my investments in a way I hadn’t initially planned.A lot of these opportunities came from contacts I made over time.

Wouldnt you think the agent would have offered it to their established client base and it would have been scooped up right from the beginning from a local investor ?

This gives them significant control and security.Joint Venture Agreement with Personal Guarantee: We establish a Joint Venture (JV) agreement that includes a personal guarantee, providing an additional layer of security for our investors.Memorandum Filing: We file a memorandum in the county where the property is located.

I think getting really good at one thing, establishing a network within that niche, and being able to analyze deals quickly is the key making things work.

Buying properties in solid and well established locations2.