Good contractors are a precious commodity and any investor who has spent years and tens of thousands of dollars on contractors form hell will not feel motivated to share those with a stranger on the internet.

Do I just send him a letter or text?

The town requires plans, proposed text, detailed narrative, and design guidelines before they'll accept the proposal. 

Is it better to constantly reach out to motivated seller leads or have motivated sellers reaching out to me?

It's fairly common and not unheard of, please call or text me directly and I'm happy to give some more guidance on it.

Motivation is to overcome down payment hurdle for expensive houses for STR

Rich doesn't last, successful does.You are young and motivated which is awesome, but you are chasing the wrong thing.

I'm not necessarily looking to invest in this area (probably upstate), but looking to meet people in the area I can learn from/build a like-minded community to keep me motivated.

Conduct thorough market research to identify target areas with high investor demand, distressed properties, and motivated sellers.

He's already purchased and moved into his next home and is very motivated to sell.