It was back in March 2020, just a couple months before covid lockdown hit.

His current monthly Payment Breakdown:- Principal: $314.66- Interest (3.875% rate): $578.779- Escrow: $700.79-TOTAL monthly payment: $1,594.24Estimated rental income: $1.2k - $1.6k per month.Would love to somehow capitalize on the existing fixed rate, but at his current monthly payment and the estimated rent it doesn't seem like a great opportunity for cash flow.

you want to stick to 6-24 month terms 

I am also working with a real estate agent for more than a month now, and had sign agreement with them until November.

How much is he paying you monthly to use your land?

Keep in mind, this entire process could potentially take a few months.

That being said there are also bad deals in any area, here included.I would run your numbers based on historical data from airbnb - pretty easy to check on airdna or even just going in the airbnb app and seeing not only what nightly rates look like for certain properties but what their occupancy is - from there you can estimate monthly revenue with a reasonable degree of accuracy and see if that lines up with your targeted returns.

My area inventory is about 1.6 months and not many great deals for flipping.

Amazing, I cash flow about $682/month and it's gone up about 30K since I purchased it.

My hypothesis is that I should be putting aside around $33K to cover the down payment, closing costs and about 6 months of reserves for PITI.