A 6-month term lease (NOT month to month agreement, but that's a different topic) would set you apart, and also offer flexibility to increase rent incrementally as prices continue to climb.

I have done this a couple of times.I love to go canyoneering through rivers that requires jumping rocks and climbing using ropes to get through.  

I would not be surprised if it continues to climb for a couple more years then settled down to 2013/2014 levels.The rental market has always been very stable here, even through the housing crisis so I feel that if I buy an investment property now, even if the price is inflated, the rental income will be a good hedge against the coming correction.Now I'm certainly no RE pro, far from it, so these are just my observations based on living here for 30+ years, so take it with a grain of salt.

The down side is that HELOCs are generally variable rates so when things turn your payments are going to climb.

Another aspect you mention is that you know it will be an uphill climb. 

I didnt see any signs of foundational cracking/major water damage/and the roof didnt have major visible wear and tear (I didnt climb up there).

Reminds me of many other successful folks in every respective industry, who painstakingly climbed the unpaved steps - becoming comfortable with being uncomfortable.Great transparency - that's the part of the "overnight success story" not many have a glimpse into - the stress and struggles that etched the success.

That having been said, there is plenty of room for prices themselves to continue to climb in certain neighborhoods.

However, climbing through a window absolutely could land you in jail or worse.

I don't think about everything but just focus on climbing the mountains one step at a time.