@Sai Krishna Byra Since you are new at all this and also want to track your personal expenses, I suggest you start with Quicken Premier or Quicken Rental Prop Manager.

That technique works in any market so it really isn't specific to market contractions or bear real estate markets.Does anyone have any suggestion on resources for profiting from bear real estate markets?

Major undertaking to do what the engineer is suggesting.

But, the whole exercise now becomes: at what list price does this property make sense?

The person presenting me this deal is suggesting it could warrant up to $200 a night, through AirBnb. 

Great find, congrats.Don't expect him to be out in 30 days, As Jay suggests you will likely keep the 30K.

I feel reasonably equipped for what we are trying to accomplish ( financial freedom in 5 years) but wide open to suggestions, guidance, mentoring, and changing the plan as needed;when needed.   

Anyway, I wanted to put a few details out to the community to see if anyone has any suggestions:1.

If you don't have experience in development, I would suggest finding someone experienced this is a highly risky venture.

Thanks for all the suggestions!