Contact the college sports department and music department ASAP.

I am looking at houses near our local mountain where tons of local tourism flows through for winter and summer sports.

We have sporting and cultural events that attract people year-round, while our high season (January through March/April) attracts our highest rental rates.

I want to grow local endurance sports and promote cycling/bicycles.

The only thing that matters is how much you're willing to gamble.

There's no "best way" to accomplish this and it's a gamble every time.

You shouldn't be spending it, gambling it, or investing it.

If you can't buy the property right it's a gamble, not an investment. 

does not mean this will also happen to you.So this is what you do.YOU need to do a cost/deal calculation for every method for lead generation you are considering for your market.Now you know how much money you need IF you were to do DMM, or IF you were to do bandit signs.Now this is DATA, so you are not gambling much here.Then factor in the effort it takes and the time it takes for a deal.Bandit signs may be almost free but it is illegal and a LOT of effort and work, and again risk for hefty fines.DMM simply is a bad idea... so figure out what is feasible and then you go for that!

You are taking a gamble because a bad tenant could cost you way more than appreciation, once you subtract out the transaction costs.