I had a similar situation with established snow birds renting Dec 15 to March 31 for a price that had not been adjusted for over 5 years.

Without payoff and lien info, this is a complete gamble for you, IMO.

At the moment it looks more like gambling.

Trying to establish my team so any recommendations for realtors, contractors, lenders, etc will be appreciated! 

Typically when getting checkbook control you will have a higher establishment fee but less ongoing fees and delays when having to go through the custodian each time you need to perform a transaction.  

For the past 8 years, I've faced numerous struggles while trying to establish a new life on my own.

We only accept good funds (money order/cashier's check) for the initial payment, and then we do electronic once the relationship has been established.

Gains through crypto felt uncertain to me but still had a draw, so I decided I wouldn't use more than 5% of my disposable income to gamble (whether on leveraged index funds like QLD or crypto).

Is it a gamble to move into one of these neighborhoods if the market crashes?

With an established rental income on the existing property and more appealing cash flow the bank would find us more eligible for a loan at that time.