But it's playing with fire to buy there if STR is a priority as it's very likely they will eventually start enforcing it better.

Remember EVERY "deal" or sold property started as an off-market whatever.

I didn't have much imagination for it. 5 years ago I started looking at buying a larger home I could house hack because it allowed me to get a larger property than I could afford.

You can start to educate yourself on the individual components; how much does it cost to paint on a per sqft basis or what is an average kitchen remodel.  

I have been reading the online resources about getting started, searching the market, and even doing tours, but I am hesitant to jump in and buy a house as I have quite a large amount of student debt.

I started with $25k and I bought the cheapest distressed 2/1 SFH I could afford. 

Start with VRBO and Airbnb and use their iCal function to sync calendars. 

As someone who wants to avoid starting over, I’m extremely cautious about who I partner with.

Attend your local REIA and start connecting.  

Would greatly appreciate advise on how to start sourcing the land and/or connect me to land brokers who can help.Thank you in advance!